CN110615758B - 具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法 - Google Patents
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000004220 aggregation Methods 0.000 title claims abstract description 35
- 230000002776 aggregation Effects 0.000 title claims abstract description 35
- 230000000694 effects Effects 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 54
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 30
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000047 product Substances 0.000 claims abstract description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 18
- 239000003480 eluent Substances 0.000 claims abstract description 18
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 13
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011259 mixed solution Substances 0.000 claims abstract description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 11
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims abstract description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000012043 crude product Substances 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 9
- 239000012046 mixed solvent Substances 0.000 claims abstract description 9
- 239000012044 organic layer Substances 0.000 claims abstract description 9
- 239000003208 petroleum Substances 0.000 claims abstract description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004327 boric acid Substances 0.000 claims abstract description 4
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 claims description 7
- YWYRVWBEIODDTJ-UHFFFAOYSA-N 1-ethenyl-9h-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C(C=C)=CC=C2 YWYRVWBEIODDTJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 8
- 238000010025 steaming Methods 0.000 abstract 1
- 238000002390 rotary evaporation Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000001514 detection method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 1
- 238000011953 bioanalysis Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000002866 fluorescence resonance energy transfer Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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Abstract
本发明公开了具有聚集诱导发光效应的9‑二(4‑吡啶)乙烯‑芴的制备方法。9‑芴酮、四溴化碳与三苯基膦溶解在无水二氯甲烷中,在氮气保护下加热搅拌反应,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9‑二溴乙烯‑芴,然后将9‑二溴乙烯‑芴与4‑吡啶硼酸溶解在1,4‑二氧六环与水的混合溶液中,加入无水碳酸钠、三苯基膦和醋酸钯催化剂,在氮气保护下加热搅拌反应,反应结束后,用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物9‑二(4‑吡啶)乙烯‑芴。本发明的优点为:制备方法简单,产物具有明显的聚集诱导发光效应,是一个具有广泛应用价值的新材料。
Description
一技术领域
本发明涉及具有聚集诱导发光效应的有机化合物的制备方法,具体涉及9-二(4-吡啶)乙烯-芴的制备方法。
二背景技术
聚集诱导发光效应是指在分子在在稀溶液中或分散态时具有很弱甚至无荧光发射,而在聚集态或固态时荧光发射明显增强。聚集诱导发光材料的出现缓解了传统发光材料固态发光效率低的问题,从而受到了广泛的关注。到目前为止,聚集诱导发光材料在传感和生物分析等方面具有广泛应用。聚集诱导发光材料在传感领域的一个重要应用是对爆炸物的检测(Polym.Chem,2016,7,6309-6317),主要检测机理是激发态的电荷转移或者荧光共振能量转移。除此之外,聚集诱导发光材料在生物医学分析、成像甚至是治疗方面都发挥着重要的作用(Sci.China.Chem,2016,59,1609-1615)。经过十几年的发展,聚集诱导发光材料受到了越来越多研究者的重视,已然成为一个热门的研究领域。
三发明内容
本发明目的在于提供具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法。
该有机化合物具有明显的聚集诱导发光效应,在良性溶剂N,N’-二甲基甲酰胺中该有机化合物的发光很弱,但在不良溶剂水中该有机化合物的发光很强。
实现本发明包括以下步骤:
1.1,9-芴酮、四溴化碳与三苯基膦溶解在无水二氯甲烷中,在氮气保护下搅拌加热至30~60℃反应12~36小时,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9-二溴乙烯-芴;
1.2,将9-二溴乙烯-芴与4-吡啶硼酸溶解在1,4-二氧六环与水的混合溶液中,加入无水碳酸钠、三苯基膦和醋酸钯催化剂,在氮气保护下搅拌加热至100~140℃反应10~20小时,反应结束后,用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物9-二(4-吡啶)乙烯-芴。
本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法步骤1.1中,9-芴酮、四溴化碳与三苯基膦的摩尔比为1:2~4:3~5。
本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法步骤1.1中,20mmol 9-芴酮对应的无水二氯甲烷的体积为60~140mL。
本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法步骤1.2中,9-二溴乙烯-芴、4-吡啶硼酸、无水碳酸钠、三苯基膦、醋酸钯的摩尔比为1:1~5:4~6:0.2~1:0.1~1。
本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法步骤1.2中,1mmol 9-二溴乙烯-芴对应的1,4-二氧六环与水的混合溶液体积为40~60mL。
本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法步骤1.2中,1,4-二氧六环与水的体积比为1:0.125~0.5。
本申请提供了具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法,其制备方法简单,产物具有明显的聚集诱导发光效应,是一个具有广泛应用价值的新材料。
四具体实施方式
下面结合附图和具体实施例对本发明技术方案作进一步详细描述,所描述的具体实施例仅对本发明进行解释说明,并不用以限制本发明。
实施例1:本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备的,包括以下步骤:
第一步,9-芴酮(3.604g,20.0mmol),四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)溶解在100mL无水二氯甲烷中,在氮气保护下搅拌加热至40℃反应24小时,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9-二溴乙烯-芴;
第二步,将9-二溴乙烯-芴(338mg,1.00mmol)与4-吡啶硼酸(615mg,5.00mmol)溶解在50mL 1,4-二氧六环与水(V:V=1:0.25)的混合溶液中,加入无水碳酸钠(690mg,5.00mmol)、三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂,在氮气保护下搅拌加热至110℃反应12小时,反应结束后用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物9-二(4-吡啶)乙烯-芴。
实施例2:本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备的,包括以下步骤:
第一步,9-芴酮(3.604g,20.0mmol),四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)溶解在80mL无水二氯甲烷中,在氮气保护下搅拌加热至40℃反应24小时,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9-二溴乙烯-芴;
第二步,将9-二溴乙烯-芴(338mg,1.00mmol)与4-吡啶硼酸(615mg,5.00mmol)溶解在50mL 1,4-二氧六环与水(V:V=1:0.25)的混合溶液中,加入无水碳酸钠(690mg,5.00mmol)、三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂,在氮气保护下搅拌加热至110℃反应12小时,反应结束后用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物9-二(4-吡啶)乙烯-芴。
实施例3:本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备的,包括以下步骤:
第一步,9-芴酮(3.604g,20.0mmol),四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)溶解在80mL无水二氯甲烷中,在氮气保护下搅拌加热至40℃反应20小时,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9-二溴乙烯-芴;
第二步,将9-二溴乙烯-芴(338mg,1.00mmol)与4-吡啶硼酸(615mg,5.00mmol)溶解在50mL 1,4-二氧六环与水(V:V=1:0.25)的混合溶液中,加入无水碳酸钠(690mg,5.00mmol)、三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂,在氮气保护下搅拌加热至110℃反应12小时,反应结束后用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物9-二(4-吡啶)乙烯-芴。
实施例4:本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备的,包括以下步骤:
第一步,9-芴酮(3.604g,20.0mmol),四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)溶解在80mL无水二氯甲烷中,在氮气保护下搅拌加热至40℃反应24小时,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9-二溴乙烯-芴;
第二步,将9-二溴乙烯-芴(338mg,1.00mmol)与4-吡啶硼酸(615mg,5.00mmol)溶解在60mL 1,4-二氧六环与水(V:V=1:0.25)的混合溶液中,加入无水碳酸钠(690mg,5.00mmol)、三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂,在氮气保护下搅拌加热至110℃反应12小时,反应结束后用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物9-二(4-吡啶)乙烯-芴。
实施例5:本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备的,包括以下步骤:
第一步,9-芴酮(3.604g,20.0mmol),四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)溶解在100mL无水二氯甲烷中,在氮气保护下搅拌加热至40℃反应24小时,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9-二溴乙烯-芴;
第二步,将9-二溴乙烯-芴(338mg,1.00mmol)与4-吡啶硼酸(615mg,5.00mmol)溶解在50mL 1,4-二氧六环与水(V:V=1:0.25)的混合溶液中,加入无水碳酸钠(690mg,5.00mmol)、三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂,在氮气保护下搅拌加热至120℃反应12小时,反应结束后用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物9-二(4-吡啶)乙烯-芴。
实施例6:本发明具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备的,包括以下步骤:
第一步,9-芴酮(3.604g,20.0mmol),四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)溶解在100mL无水二氯甲烷中,在氮气保护下搅拌加热至45℃反应30小时,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9-二溴乙烯-芴;
第二步,将9-二溴乙烯-芴(338mg,1.00mmol)与4-吡啶硼酸(615mg,5.00mmol)溶解在50mL 1,4-二氧六环与水(V:V=1:0.25)的混合溶液中,加入无水碳酸钠(690mg,5.00mmol)、三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂,在氮气保护下搅拌加热至120℃反应12小时,反应结束后用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物9-二(4-吡啶)乙烯-芴。
附图说明
图1,具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的核磁谱图。
图2,具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的固体荧光激发、发射谱图。
图3,具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴在DMF和水的混合溶液中的荧光发射光谱图。
Claims (6)
1.具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法,包括以下步骤:
1.1,9-芴酮、四溴化碳与三苯基膦溶解在无水二氯甲烷中,在氮气保护下搅拌加热至30~60℃反应12~36小时,反应结束后,采用层析法,以正己烷为洗脱剂,得到粗产物,最后用正己烷重结晶得到黄色产物9-二溴乙烯-芴;
1.2,将9-二溴乙烯-芴与4-吡啶硼酸溶解在1,4-二氧六环与水的混合溶液中,加入无水碳酸钠、三苯基膦和醋酸钯催化剂,在氮气保护下搅拌加热至100~140℃反应10~20小时,反应结束后,用乙酸乙酯萃取3遍,收集有机层,用无水硫酸钠干燥,减压旋蒸,采用层析法,以乙酸乙酯与石油醚的混合溶剂(V:V=1:1)为洗脱剂得到淡黄色产物。
2.根据权利要求1所述的具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法,其特征在于步骤1.1中9-芴酮与四溴化碳与三苯基膦的摩尔比为1:2~4:3~5。
3.根据权利要求1所述的具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法,其特征在于步骤1.1中20mmol 9-芴酮对应的无水二氯甲烷的体积为60~140mL。
4.根据权利要求1所述的具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法,其特征在于步骤1.2中9-二溴乙烯-芴、4-吡啶硼酸、无水碳酸钠、三苯基膦与醋酸钯的摩尔比为1:1~5:4~6:0.2~1:0.1~1。
5.根据权利要求1所述的具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法,其特征在于步骤1.2中1mmol 9-二溴乙烯-芴对应的1,4-二氧六环与水的混合溶液体积为40~60mL。
6.根据权利要求1所述的具有聚集诱导发光效应的9-二(4-吡啶)乙烯-芴的制备方法,其特征在于步骤1.2中1,4-二氧六环与水的体积比为1:0.125~0.5。
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