CN110734395B - 具有聚集诱导发光效应的9-二(3-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 33
- 230000002776 aggregation Effects 0.000 title claims abstract description 33
- 238000004220 aggregation Methods 0.000 title claims abstract description 33
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- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 69
- 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 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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 20
- 239000000047 product Substances 0.000 claims abstract description 18
- 238000004440 column chromatography Methods 0.000 claims abstract description 16
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 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 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 10
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims abstract description 10
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 claims abstract description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 8
- 239000012044 organic layer Substances 0.000 claims abstract description 8
- 239000011259 mixed solution Substances 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000003480 eluent Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 7
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- 239000003208 petroleum Substances 0.000 claims description 7
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- YWYRVWBEIODDTJ-UHFFFAOYSA-N 1-ethenyl-9h-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C(C=C)=CC=C2 YWYRVWBEIODDTJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 10
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- MEOPJXNUOJPKKX-UHFFFAOYSA-N ethene 9H-fluorene Chemical compound C=C.C1=CC=CC=2C3=CC=CC=C3CC12 MEOPJXNUOJPKKX-UHFFFAOYSA-N 0.000 abstract 1
- 238000002390 rotary evaporation Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 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
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- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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Abstract
本发明公开了具有聚集诱导发光效应的9‑二(3‑吡啶)乙烯‑芴的制备方法。将9‑芴酮、四溴化碳和三苯基膦加入二氯甲烷中加热搅拌反应，反应结束后采用柱层析法分离，重结晶得到黄色9‑二溴乙烯‑芴；将9‑二溴乙烯‑芴、3‑吡啶硼酸、无水碳酸钠、三苯基膦和醋酸钯加入1,4‑二氧六环与水的混合溶液中加热搅拌反应，反应结束后用乙酸乙酯萃取收集有机层，用无水硫酸钠干燥，减压旋蒸，采用柱层析法分离得到粗产物，再用乙酸乙酯洗涤得到淡黄色产物9‑二(3‑吡啶)乙烯‑芴。本发明的优点为：制备方法简单，产率高，反应活性好，产物具有明显的聚集诱导发光效应，是一种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(3-吡啶)乙烯-芴的制备方法。
二背景技术
聚集诱导发光是指分子在其稀溶液或分散态时不发光或者微弱发光，而在其聚集态发光显著增强的现象。相对于传统的发光材料，聚集诱导发光材料具有光稳定性高、长效追踪效果等优点，已引起研究工作者广泛的兴趣。经过十几年的发展，聚集诱导发光材料在众多材料领域得到很好的应用，如传感材料、液晶材料、光波导材料等等。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、成像甚至治疗方面展现了巨大的潜质(Sci.China.Chem,2016,59,1609-1615)。
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(3-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将9-芴酮，四溴化碳和三苯基膦加入无水二氯甲烷中，在氮气保护下加热至30～60℃，反应12～36小时，反应结束后冷却，采用柱层析法，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，3-吡啶硼酸，无水碳酸钠，三苯基膦和醋酸钯催化剂加入1,4-二氧六环与水的混合溶液中，在氮气保护下加热至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，采用柱层析法，以乙酸乙酯：石油醚(V:V＝1:1)为洗脱剂得到粗产物，再用乙酸乙酯洗涤得到淡黄色产物9-二(3-吡啶)乙烯-芴。
本发明具有聚集诱导发光效应的9-二(3-吡啶)乙烯-芴的制备方法步骤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；
本发明具有聚集诱导发光效应的9-二(3-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(3-吡啶)乙烯-芴的制备方法步骤1.2中，9-二溴乙烯-芴、3-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(3-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体积为40～60mL；
本发明具有聚集诱导发光效应的9-二(3-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(3-吡啶)乙烯-芴的制备方法，其制备方法简单，产率高，反应活性好，产物具有明显的聚集诱导发光效应，是一种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(3-吡啶)乙烯-芴的制备方法，包括以下步骤：
第一步，将9-芴酮(3.604g,20.0mmol)，四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)加入100mL无水二氯甲烷中，在氮气保护下加热至40℃反应24小时，反应结束后冷却，采用柱层析法，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)，3-吡啶硼酸(615mg,5.00mmol)，无水碳酸钠(690mg,5.00mmol)，三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂加入50mL 1,4-二氧六环与水(V:V＝4:1)的溶液中，在氮气保护下加热至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，采用柱层析法，以乙酸乙酯：石油醚(V:V＝1:1)为洗脱剂得到粗产物，再用乙酸乙酯洗涤得到淡黄色产物9-二(3-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(3-吡啶)乙烯-芴的制备方法，包括以下步骤：
第一步，将9-芴酮(3.604g,20.0mmol)，四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)加入80mL无水二氯甲烷中，在氮气保护下加热至40℃反应24小时，反应结束后冷却，采用柱层析法，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)，3-吡啶硼酸(615mg,5.00mmol)，无水碳酸钠(690mg,5.00mmol)，三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂加入50mL 1,4-二氧六环与水(V:V＝4:1)的溶液中，在氮气保护下加热至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，采用柱层析法，以乙酸乙酯：石油醚(V:V＝1:1)为洗脱剂得到粗产物，再用乙酸乙酯洗涤得到淡黄色产物9-二(3-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(3-吡啶)乙烯-芴的制备方法，包括以下步骤：
第一步，将9-芴酮(3.604g,20.0mmol)，四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)加入80mL无水二氯甲烷中，在氮气保护下加热至40℃反应20小时，反应结束后冷却，采用柱层析法，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)，3-吡啶硼酸(615mg,5.00mmol)，无水碳酸钠(690mg,5.00mmol)，三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂加入50mL 1,4-二氧六环与水(V:V＝4:1)的溶液中，在氮气保护下加热至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，采用柱层析法，以乙酸乙酯：石油醚(V:V＝1:1)为洗脱剂得到粗产物，再用乙酸乙酯洗涤得到淡黄色产物9-二(3-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(3-吡啶)乙烯-芴的制备方法，包括以下步骤：
第一步，将9-芴酮(3.604g,20.0mmol)，四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)加入80mL无水二氯甲烷中，在氮气保护下加热至40℃反应24小时，反应结束后冷却，采用柱层析法，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)，3-吡啶硼酸(615mg,5.00mmol)，无水碳酸钠(690mg,5.00mmol)，三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂加入60mL 1,4-二氧六环与水(V:V＝4:1)的溶液中，在氮气保护下加热至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，采用柱层析法，以乙酸乙酯：石油醚(V:V＝1:1)为洗脱剂得到粗产物，再用乙酸乙酯洗涤得到淡黄色产物9-二(3-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(3-吡啶)乙烯-芴的制备方法，包括以下步骤：
第一步，将9-芴酮(3.604g,20.0mmol)，四溴化碳(13.270g,40.0mmol)与三苯基膦(17.530g,80.0mmol)加入100mL无水二氯甲烷中，在氮气保护下加热至40℃反应24小时，反应结束后冷却，采用柱层析法，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)，3-吡啶硼酸(615mg,5.00mmol)，无水碳酸钠(690mg,5.00mmol)，三苯基膦(130mg,0.50mmol)和醋酸钯(128mg,0.12mmol)催化剂加入50mL 1,4-二氧六环与水(V:V＝4:1)的溶液中，在氮气保护下加热至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，采用柱层析法，以乙酸乙酯：石油醚(V:V＝1:1)为洗脱剂得到粗产物，再用乙酸乙酯洗涤得到淡黄色产物9-二(3-吡啶)乙烯-芴。
附图说明
图1.所述具有聚集诱导发光效应的9-二(3-吡啶)乙烯-芴的核磁谱图。
图2.所述具有聚集诱导发光效应的9-二(3-吡啶)乙烯-芴的固体荧光激发、发射谱图。
图3.所述具有聚集诱导发光效应的9-二(3-吡啶)乙烯-芴在DMF和水的混合溶液中的荧光图。
Claims (6)
1.具有聚集诱导发光效应的9-二(3-吡啶)乙烯-芴的制备方法，包括以下步骤:
1.1将9-芴酮，四溴化碳和三苯基膦加入无水二氯甲烷中，在氮气保护下加热至30～60℃，反应12～36小时，反应结束后冷却，采用柱层析法，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，3-吡啶硼酸，无水碳酸钠，三苯基膦和醋酸钯催化剂加入1,4-二氧六环与水的混合溶液中，在氮气保护下加热至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，采用柱层析法，以乙酸乙酯：石油醚(V:V＝1:1)为洗脱剂得到粗产物，再用乙酸乙酯洗涤得到淡黄色产物9-二(3-吡啶)乙烯-芴。
2.根据权利要求1所述的具有聚集诱导发光效应的9-二(3-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(3-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(3-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、3-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(3-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(3-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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