CN110305114A - 一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用 - Google Patents

一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用 Download PDF

Info

Publication number
CN110305114A
CN110305114A CN201810259477.XA CN201810259477A CN110305114A CN 110305114 A CN110305114 A CN 110305114A CN 201810259477 A CN201810259477 A CN 201810259477A CN 110305114 A CN110305114 A CN 110305114A
Authority
CN
China
Prior art keywords
fluorescence
pressure
anthryl
fluorescent material
aggregation inducing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201810259477.XA
Other languages
English (en)
Other versions
CN110305114B (zh
Inventor
王磊
刘威
穆广园
庄少卿
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
WUHAN SHANGSAI PHOTOELECTRIC TECHNOLOGY Co Ltd
Original Assignee
WUHAN SHANGSAI PHOTOELECTRIC TECHNOLOGY Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by WUHAN SHANGSAI PHOTOELECTRIC TECHNOLOGY Co Ltd filed Critical WUHAN SHANGSAI PHOTOELECTRIC TECHNOLOGY Co Ltd
Priority to CN201810259477.XA priority Critical patent/CN110305114B/zh
Publication of CN110305114A publication Critical patent/CN110305114A/zh
Application granted granted Critical
Publication of CN110305114B publication Critical patent/CN110305114B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/38—[b, e]-condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

本发明公开了一类具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料。该类材料可通过简单的耦合反应制得，其在有机溶剂中具有较好的溶解性，而在水中几乎不溶解，在水和有机溶剂中可以形成纳米聚集态，具有良好的聚集诱导荧光特性。同时通过研磨该类材料的固态粉末，该类材料的荧光发射波长会向长波方向移动，用二氯甲烷熏蒸后荧光发射波长则会恢复，再研磨时该类材料的荧光发射波长依然会向长波方向移动，采用加热的方法该类材料的荧光发射波长则会恢复，具有可回复的压致荧光变色性能。具有压致荧光变色性质的荧光材料是一种新型的智能材料，它在复写纸、密写纸和机械力传感方面有着非常重要的应用。

Description

一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料 及其应用
技术领域
本发明属于荧光材料技术领域，特别涉及一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用。
背景技术
荧光材料由于其在光电器件、环境传感器、生物科学等领域具有重大的应用价值，近年来引起了科学家们的极大关注。传统的荧光材料在溶液态时发光较强，在聚集态下会发生聚集淬灭即ACQ，这大大限制了这类材料的实际应用。2001年，唐本忠课题组设计合成一种新型的硅杂环戊二烯类化合物，他们发现该化合物在溶液中时几乎不发光，而在聚集态下化合物发光较强，他们将这种现象命名为聚集诱导荧光(AIE)，AIE的发现为共轭有机发光材料的实际应用拓宽了道路，随后他们对AIE的机理进行了深入的研究，目前普遍认为具有AIE效应的分子在溶液态时处于单分子状态，由于分子内某两种基团的相互作用导致了分子扭曲，这种扭曲作用在光激发的作用下会产生剧烈的扭摆运动，会耗散大量的能量，因而发出的荧光减弱。而在聚集态或固态下，由于分子的适当堆积，这种扭摆运动就受到了限制，受光激发时，主要能量都用于发光，因此表现出很强的荧光特性。
随着对AIE材料的不断研究，具有AIE性质的材料在荧光传感、有机电致发光二极管和压致荧光变色等方面的实际应用也得到了很大程度的发展。由于大多数具有AIE性质的化合物具有扭曲的分子构象，导致分子堆积相对松散，在受到外界刺激时由于堆积方式的改变会呈现不同的发光行为，即压致荧光变色性质。压致荧光变色(piezofluoro-chromism,PFC)是指化合物在机械力作用下，如研磨、剪切、压力等，其荧光光色发生明显变化的一种现象。具有压致荧光变色性质的荧光材料是一种新型的智能材料，它在复写纸、密写纸和机械力传感方面有着非常重要的应用。但是目前为止已经报道的具有压致荧光变色的荧光材料还不是很多，所以设计合成新型的具有压致变色性质的聚集诱导发光材料仍然被迫切需要。
发明内容
为解决以上技术问题，本发明提供了一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料，其特征在于，其结构通式如下列结构式：
其中，D为给电子基团；A为吸电子基团。
优选的，所述D是下列取代或未取代的基团2a～2h中的任意一种：
其中，*为与蒽连接的位点。
优选的，所述A是下列取代或未取代的基团3a～3f中的任意一种：
其中，*为与蒽连接的位点。
优选的，所述蒽基荧光材料为下列化合物中的任一种：
以上所示化合物1-48是符合本发明精神和原则的代表结构，应当理解，列出以上化合物的具体结构，只是为了更好地解释本发明，并非是对本发明的限制。
本发明还提供了一种上述具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料的制备方法，包括以下路线：
第一步：
第二步：
其中，D为给电子基团；A为吸电子基团。
具体的，所述第一步中，9-溴蒽和A-B(OH)2按照摩尔比例0.8～0.85比例投料，Suzuki反应的具体反应条件为：辅助原料包括四-三苯基磷钯、碳酸钾、乙醇和甲苯，所述四-三苯基磷钯与所述9-蒽硼酸的摩尔比例为1:169～1:170,当所述碳酸钾的浓度2Mol/L时，所述碳酸钾、乙醇和甲苯的体积比为1:1:2；
则所述第二步中，A取代蒽基和NBS(氮溴代丁二酰亚胺)按照摩尔比例0.8～0.85投料，A取代溴化蒽与D-B(OH)2按照摩尔比例0.8～0.85投料，Suzuki反应的具体反应条件为：辅助原料包括四-三苯基磷钯、碳酸钾、乙醇和甲苯，所述四-三苯基磷钯与所述D-B(OH)2的摩尔比例为0.01～0.02,当所述碳酸钾的浓度2Mol/L时，所述碳酸钾、乙醇和甲苯的体积比为1:1:2；
或者，
所述第一步中，9-蒽硼酸和A-Br按照摩尔比例0.9～0.95比例投料，Suzuki反应的具体反应条件为：辅助原料包括四-三苯基磷钯、碳酸钾、乙醇和甲苯，所述四-三苯基磷钯与所述9-溴蒽的摩尔比例为1:195～1:196,当所述碳酸钾的浓度2Mol/L时，所述碳酸钾、乙醇和甲苯的体积比为1:1:2；
则所述第二步中，A取代蒽基和NBS(氮溴代丁二酰亚胺)按照摩尔比例0.8～0.85投料，A取代溴化蒽与D-B(OH)2按照摩尔比例0.9～1.0投料，Suzuki反应的具体反应条件为：辅助原料包括四-三苯基磷钯、碳酸钾、乙醇和甲苯，所述四-三苯基磷钯与所述D-B(OH)2的摩尔比例为0.02～0.03,当所述碳酸钾的浓度2Mol/L时，所述碳酸钾、乙醇和甲苯的体积比为1:1:2。
本发明还提供了一种上述具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料的应用，所述蒽基荧光材料用于制作传感器和/或光电功能器件。
本发明的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料可以通过简单的耦合反应制得。本发明的荧光材料在普通的有机溶剂中都具有很好的溶解性，而在水中几乎不溶解，在水和有机溶剂中可以形成纳米聚集态，具有良好的聚集诱导荧光特性。同时通过研磨该类材料的固态粉末该类材料的荧光发射波长会向长波方向移动，用二氯甲烷熏蒸后荧光发射波长则会恢复，再研磨时该类材料的荧光发射波长依然会向长波方向移动，采用加热的方法该类材料的荧光发射波长则会恢复，具有可回复的压致荧光变色性能。具有压致荧光变色性质的荧光材料是一种新型的智能材料，它在复写纸、密写纸和机械力传感方面有着非常重要的应用。
附图说明
图1为本发明化合物1在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质；
图2为本发明化合物1在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质；
图3为本发明化合物7在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质；
图4为本发明化合物7在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质；
图5为本发明化合物13在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质；
图6为本发明化合物13在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质。
具体实施方式
下面结合实施例对本发明做进一步说明。依据本发明的技术实质对以下实施例所作的任何简单修改、等同变化等，仍属于本发明技术方案的保护范围。本发明不限于以下实施例中所述的内容。
实施例1
反应路线如下：
2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将10.00g 9-蒽硼酸(45.03mmol)和13.26g 2-氯-4,6-二苯基-1,3,5-三嗪(49.54mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物17.55g。(产率：95.17％)
2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将15.00g 2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪(36.66mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物16.68g。(产率：93.18％)
化合物1的合成：
将1.29g 4-硼酸-9-苯基咔唑(4.50mmol)和2.00g 2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪(4.10mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.40g。(产率：90.05％)
将化合物1加入含有不同比例的四氢呋喃和水的溶剂中，研究其聚集诱导效应。图1所示，化合物1在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质，从图中可以看出随着不良溶剂水的加入，其荧光强度逐渐增强，表明该化合物1具有明显的聚集诱导荧光性质。
连续对化合物1进行研磨、热恢复和溶剂熏蒸等操作，研究其压致荧光变色性质。图2所示，本实施例化合物1在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质，从图中可以看出当对化合物进行研磨时其荧光光色发生明显的红移，而研磨后进行溶剂熏蒸化合物的光色回复原来的荧光光色，再对化合物进行研磨其荧光光色再次发生红移，再研磨的样品进行加热后化合物的光色回复到原来的荧光光色，表明该化合物具有可回复的压致荧光变色性质。
实施例2
反应路线如下：
2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将10.00g 9-蒽硼酸(45.03mmol)和13.26g 2-氯-4,6-二苯基-1,3,5-三嗪(49.54mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物17.55g。(产率：95.17％)
2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将15.00g 2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪(36.66mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物16.68g。(产率：93.18％)
化合物7的合成：
将1.29g 9-苯基咔唑-3-硼酸(4.50mmol)和2.00g 2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪(4.10mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.40g。(产率：90.05％)
将化合物7加入含有不同比例的四氢呋喃和水的溶剂中，研究其聚集诱导效应。图3所示，化合物7在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质，从图中可以看出随着不良溶剂水的加入，其荧光强度逐渐增强，表明该化合物7具有明显的聚集诱导荧光性质。
连续对化合物7进行研磨、热恢复和溶剂熏蒸等操作，研究其压致荧光变色性质。图4所示，本实施例化合物7在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质，从图中可以看出当对化合物进行研磨时其荧光光色发生明显的红移，而研磨后进行溶剂熏蒸化合物的光色回复原来的荧光光色，再对化合物进行研磨其荧光光色再次发生红移，再研磨的样品进行加热后化合物的光色回复到原来的荧光光色，表明该化合物7具有可回复的压致荧光变色性质。
实施例3
反应路线如下：
2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将10.00g 9-蒽硼酸(45.03mmol)和13.26g 2-氯-4,6-二苯基-1,3,5-三嗪(49.54mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物17.55g。(产率：95.17％)
2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将15.00g 2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪(36.66mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物16.68g。(产率：93.18％)
化合物13的合成：
将1.29g 3-硼酸-9-苯基咔唑(4.50mmol)和2.00g 2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪(4.10mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.40g。(产率：90.05％)
将化合物13加入含有不同比例的四氢呋喃和水的溶剂中，研究其聚集诱导效应。图5所示，化合物13在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质，从图中可以看出随着不良溶剂水的加入，其荧光强度逐渐增强，表明该化合物13具有明显的聚集诱导荧光性质。
连续对化合物13进行研磨、热恢复和溶剂熏蒸等操作，研究其压致荧光变色性质。图6所示，本实施例化合物13在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质，从图中可以看出当对化合物进行研磨时其荧光光色发生明显的红移，而研磨后进行溶剂熏蒸化合物的光色回复原来的荧光光色，再对化合物进行研磨其荧光光色再次发生红移，再研磨的样品进行加热后化合物的光色回复到原来的荧光光色，表明该化合物13具有可回复的压致荧光变色性质。
实施例4
反应路线如下：
4-(9-蒽基)苯甲腈：
将10.00g 9-溴蒽(38.89mmol)和6.85g对氰基苯硼酸(46.67mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物10.00g。(产率：92.08％)
4-(9-溴化蒽)苯甲腈的合成：
将10.00g 4-(9-蒽基)苯甲腈(35.80mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物12.11g。(产率：94.46％)
化合物6的合成：
将2.00g 4-硼酸-9-苯基咔唑(6.97mmol)和2.08g 4-(9-溴化蒽)苯甲腈的合成(5.80mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.88g。(产率：95.36％)
实施例5
反应路线如下：
4-(9-蒽基)苯甲腈：
将10.00g 9-溴蒽(38.89mmol)和6.85g对氰基苯硼酸(46.67mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物10.00g。(产率：92.08％)
4-(9-溴化蒽)苯甲腈的合成：
将10.00g 4-(9-蒽基)苯甲腈(35.80mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物12.11g。(产率：94.46％)
化合物12的合成：
将2.00g 9-苯基咔唑-3-硼酸(6.97mmol)和2.08g 4-(9-溴化蒽)苯甲腈的合成(5.80mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.88g。(产率：95.36％)
实施例6
反应路线如下：
4-(9-蒽基)苯甲腈：
将10.00g 9-溴蒽(38.89mmol)和6.85g对氰基苯硼酸(46.67mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物10.00g。(产率：92.08％)
4-(9-溴化蒽)苯甲腈的合成：
将10.00g 4-(9-蒽基)苯甲腈(35.80mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物12.11g。(产率：94.46％)
化合物18的合成：
将2.00g 3-硼酸-9-苯基咔唑(6.97mmol)和2.08g 4-(9-溴化蒽)苯甲腈的合成(5.80mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.88g。(产率：95.36％)
实施例7
蒽基荧光材料用于制作传感器和/或光电功能器件。
例如，用以检测离子、气体、有机小分子、爆炸物、蛋白、酶等化学/生物传感器，向传统的聚集引起猝灭化合物引入该材料，制备高效固态发光器件等。
尽管结合实施例对本发明进行了说明，但本发明并不局限于上述实施例，应当理解，在本发明构思的引导下，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (6)

1.一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料，其特征在于，其结构通式如下列结构式：
其中，D为给电子基团；A为吸电子基团。
2.根据权利要求1所述的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料，其特征在于，所述D是下列基团2a～2h中的任意一种：
其中，*为与蒽连接的位点。
3.根据权利要求1所述的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料，其特征在于，所述A是下列取代或未取代的基团3a～3f中的任意一种：
其中，*为与蒽连接的位点。
4.根据权利要求1所述的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料，其特征在于，所述蒽基荧光材料为下列化合物中的任一种：
5.一种如权利要求1至4任一项所述的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料的制备方法，其特征在于，合成路线为：
第一步：
或者
第二步：
其中，D为给电子基团；A为吸电子基团。
6.一种如权利要求1至4任一项所述的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料的应用，其特征在于，所述蒽基荧光材料用于制作传感器和/或光电功能器件。
CN201810259477.XA 2018-03-27 2018-03-27 一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用 Active CN110305114B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810259477.XA CN110305114B (zh) 2018-03-27 2018-03-27 一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810259477.XA CN110305114B (zh) 2018-03-27 2018-03-27 一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用

Publications (2)

Publication Number Publication Date
CN110305114A true CN110305114A (zh) 2019-10-08
CN110305114B CN110305114B (zh) 2020-10-09

Family

ID=68074161

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810259477.XA Active CN110305114B (zh) 2018-03-27 2018-03-27 一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用

Country Status (1)

Country Link
CN (1) CN110305114B (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111303009A (zh) * 2018-12-12 2020-06-19 华中科技大学 一种具有高效率、低滚降的蒽基深蓝光有机电致发光材料
CN112010854A (zh) * 2020-09-07 2020-12-01 浙江大学 一种Tr*ger’s碱衍生物及其制备方法和机械诱导荧光增强特性的测试方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101225298A (zh) * 2007-01-18 2008-07-23 中国科学院化学研究所 空穴传输型蓝色发光材料及制备和应用
CN103539751A (zh) * 2013-10-17 2014-01-29 南京大学 一类均三嗪衍生物及其在有机电致发光器件中的应用
WO2016052819A1 (ko) * 2014-10-01 2016-04-07 가톨릭대학교 산학협력단 유기 광전자 소자용 화합물 및 이를 포함하는 유기 광전자 소자
CN106187817A (zh) * 2016-07-29 2016-12-07 陕西师范大学 具有聚集诱导发光性质和压致变色性质的荧光材料
CN107602469A (zh) * 2017-10-30 2018-01-19 江西科技师范大学 一种具有聚集诱导发光增强、溶剂变色和自恢复力致变色性质的萘酰亚胺化合物与应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101225298A (zh) * 2007-01-18 2008-07-23 中国科学院化学研究所 空穴传输型蓝色发光材料及制备和应用
CN103539751A (zh) * 2013-10-17 2014-01-29 南京大学 一类均三嗪衍生物及其在有机电致发光器件中的应用
WO2016052819A1 (ko) * 2014-10-01 2016-04-07 가톨릭대학교 산학협력단 유기 광전자 소자용 화합물 및 이를 포함하는 유기 광전자 소자
CN106187817A (zh) * 2016-07-29 2016-12-07 陕西师范大学 具有聚集诱导发光性质和压致变色性质的荧光材料
CN107602469A (zh) * 2017-10-30 2018-01-19 江西科技师范大学 一种具有聚集诱导发光增强、溶剂变色和自恢复力致变色性质的萘酰亚胺化合物与应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
管成飞等: "含吡啶端基9,10-双芳基蒽共轭分子的合成、聚集诱导荧光增强及双光子诱导荧光", 《有机化学》 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111303009A (zh) * 2018-12-12 2020-06-19 华中科技大学 一种具有高效率、低滚降的蒽基深蓝光有机电致发光材料
CN111303009B (zh) * 2018-12-12 2022-02-15 华中科技大学 一种具有高效率、低滚降的蒽基深蓝光有机电致发光材料
CN112010854A (zh) * 2020-09-07 2020-12-01 浙江大学 一种Tr*ger’s碱衍生物及其制备方法和机械诱导荧光增强特性的测试方法
CN112010854B (zh) * 2020-09-07 2021-07-23 浙江大学 一种Tröger’s碱衍生物及其制备方法和机械诱导荧光增强特性的测试方法

Also Published As

Publication number Publication date
CN110305114B (zh) 2020-10-09

Similar Documents

Publication Publication Date Title
Yuan et al. Synergy between twisted conformation and effective intermolecular interactions: strategy for efficient mechanochromic luminogens with high contrast
Zhao et al. Aggregation-induced emission and efficient solid-state fluorescence from tetraphenylethene-based N, C-chelate four-coordinate organoborons
Li et al. 1, 2, 5‐triphenylpyrrole derivatives with dual intense photoluminescence in both solution and the solid state: solvatochromism and polymorphic luminescence properties
Gao et al. Enhanced Sensitivity and Piezochromic Contrast through Single‐Direction Extension of Molecular Structure
Zhou et al. Effects of cyano groups on the properties of thiazole-based β-ketoiminate boron complexes: aggregation-induced emission and mechanofluorochromism
Hu et al. Effect of ionic interaction on the mechanochromic properties of pyridinium modified tetraphenylethene
Bu et al. Synthesis and piezochromic luminescence of aggregation-enhanced emission 9, 10-bis (N-alkylcarbazol-2-yl-vinyl-2) anthracenes
Lou et al. Enhanced Solution and Solid‐State Emission and Tunable White‐Light Emission Harvested by Supramolecular Approaches
Bartoloni et al. Photophysics and hydrolytic stability of betalains in aqueous trifluoroethanol
CN105906624A (zh) 一类对苯胺和邻甲苯胺气体有传感功能的荧光化合物及其荧光传感薄膜制备和应用
CN110305114A (zh) 一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用
CN108559484B (zh) 一种烷基溴代咔唑衍生物室温磷光材料及其制备和应用
Hengchang et al. Triphenylamine-decorated BODIPY fluorescent probe for trace detection of picric acid
Zhang et al. Fluorescence modulation in tribranched switchable [4] rotaxanes
Wang et al. A Mechanically Interlocked [3] Rotaxane as a Light‐Harvesting Antenna: Synthesis, Characterization, and Intramolecular Energy Transfer
Mao et al. Non-conjugated dendrimers with a porphyrin core and coumarin chromophores as peripheral units: Synthesis and photophysical properties
Liang et al. New Anthracene Derivatives as Triplet Acceptors for Efficient Green‐to‐Blue Low‐Power Upconversion
Yang et al. Synthesis of a [2] rotaxane operated in basic environment
Qu et al. The Aggregation Regularity Effect of Multiarylpyrroles on Their Near‐Infrared Aggregation‐Enhanced Emission Property
Wang et al. Tetraphenylethene-containing cruciform luminophores with aggregation-induced emission and mechanoresponsive behavior
Liu et al. Tetraphenylethene modified [n] rotaxanes: synthesis, characterization and aggregation-induced emission behavior
Li et al. Extended Fluorochromism of Anthracene Trimers with a meta‐Substituted Triphenylamine or Triphenylphosphine Core
Yang et al. A controllable chiral molecular machine: movement on molecular level
CN110016335A (zh) 一种具有醚键的纯有机室温磷光材料及其制备方法和应用
Liu et al. AIEgens with bright mechanoluminescence and thermally activated delayed fluorescence derived from (9H-carbazol-9-yl)(phenyl) methanone

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant