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含五苯基吡咯侧基聚丙烯酸酯的制备及其聚集诱导发光增强性能
增强出版Synthesis and Aggregation-enhanced Emission of Polymethacrylate with Pentaphenylpyrrole Side Group
- 高分子学报 2017年第8期 页码：1285-1293
- 作者机构：
1.北京理工大学化学学院 北京 100081
2.北京理工大学材料学院 北京 100081
- 作者简介：
支俊格, E-mail:jungezhi@bit.edu.cn Jun-ge Zhi, E-mail:jungezhi@bit.edu.cn
董宇平, E-mail:chdongyp@bit.edu.cn Yu-ping Dong, E-mail:chdongyp@bit.edu.cn
- 基金信息：国家自然科学基金(21374010)
DOI：10.11777/j.issn1000-3304.2017.17001
中图分类号：纸质出版日期：2017-8，
收稿日期：2017-1-2，
修回日期：2017-2-10，
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杨佩佩, 董立超, 李园园, 张龙龙, 石建兵, 支俊格, 佟斌, 董宇平. 含五苯基吡咯侧基聚丙烯酸酯的制备及其聚集诱导发光增强性能[J]. 高分子学报, 2017,(8):1285-1293.
Yang Pei-pei, Dong Li-chao, Li Yuan-yuan, Zhang Long-long, Shi Jian-bing, Zhi Jun-ge, Tong Bin, Dong Yu-ping. Synthesis and Aggregation-enhanced Emission of Polymethacrylate with Pentaphenylpyrrole Side Group[J]. Acta Polymerica Sinica, 2017,(8):1285-1293.
杨佩佩, 董立超, 李园园, 张龙龙, 石建兵, 支俊格, 佟斌, 董宇平. 含五苯基吡咯侧基聚丙烯酸酯的制备及其聚集诱导发光增强性能[J]. 高分子学报, 2017,(8):1285-1293. DOI： 10.11777/j.issn1000-3304.2017.17001.
Yang Pei-pei, Dong Li-chao, Li Yuan-yuan, Zhang Long-long, Shi Jian-bing, Zhi Jun-ge, Tong Bin, Dong Yu-ping. Synthesis and Aggregation-enhanced Emission of Polymethacrylate with Pentaphenylpyrrole Side Group[J]. Acta Polymerica Sinica, 2017,(8):1285-1293. DOI： 10.11777/j.issn1000-3304.2017.17001.
摘要
设计合成了具有聚集诱导发光增强活性（AEE）的含五苯基吡咯的甲基丙烯酸酯单体M-PPP，并通过自由基聚合制备了系列均聚物及不同五苯基吡咯侧基含量的聚甲基丙烯酸酯共聚物.所制备的均聚物P与共聚物CP在THF/H
2
O体系中均具有AEE特性，在水含量大于20%时荧光开始增加，大于80%时荧光快速增加，95%时相对荧光强度达到最大；单体M-PPP则在水含量低于70%时荧光强度略有降低，随后迅速增加，95%后荧光强度下降.五苯基吡咯侧基含量较高的共聚物表现出更好的AEE特性.进一步的研究发现，共聚物CP在THF/H
2
O混合溶液中能够对赖氨酸产生荧光点亮型响应.
Abstract
Methacrylate monomer M-PPP
which is aggregation-enhanced emission (AEE) active and with a conjugated pentaphenylpyrrole side group
was designed and synthesized through palladium-catalyzed cyclization of arylamine and diaryl acetylene
Suzuki cross-coupling and esterification with EDCI as dehydrant. A series of homopolymers P
1
P
2
P
3
and copolymers CP
41
CP
21
CP
11
CP
12
CP
14
were prepared by free radical polymerization of M-PPP and copolymerization of M-PPP with BMA. The molar ratio of M-PPP unit and BMA unit in copolymers CPs was calculated based on the chemical shift and integrations of their CH
2
groups. The content of M-PPP units in the copolymers was lower than those in raw materials
mainly due to the low polymerization activity attributed to the bulky conjugated pentaphenylpyrrole side group. The monomer M-PPP
the polymers P
1
P
2
P
3
and the copolymers CP
41
CP
21
CP
11
were of high thermal stability with their decomposition temperature above 300℃
while the decomposition temperatures of CP
12
CP
14
decreased slightly because of the lower content of the conjugated pentaphenylpyrrole side group. Both the monomer M-PPP and the polymers exhibited obvious AEE feature in THF/H
2
O mixture. The fluorescence intensity of the polymers increased slowly when the water fraction (
f
w
) was above 20%
and it increased faster when
f
w
is above 80%. The relative fluorescence intensity (I/I
0
) reached to a maximum at
f
w
of 95%
mainly attributed to the aggregation of the conjugated luminogen pentaphenylpyrrole segment in the side-chain and the entanglement of the flexible polymer main chains in THF/H
2
O mixture
which could restrict the motion of pentaphenylpyrrole and intramolecular rotation of the benzene rings
leading to enhanced fluorescence emission. The fluorescence intensity of M-PPP decreased a little when
f
w
was lower than 70%
then increased sharply
and the maximal I/I
0
was 3.9 at
f
w
of 95%
which was higher than those of the polymers due to the lower content of conjugated pentaphenylpyrrole side group in the polymers. The copolymers CPs exhibited similar AEE behavior as the polymers P
1
P
2
P
3
in THF/H
2
O mixture
and they showed better AEE feature when increasing the content of the conjugated pentaphenylpyrrole side group. Furthermore
the copolymers CPs could "turn-on" to detect lysine selectively in THF/H
2
O mixture due to the interaction of BMA unit and lysine
and more sensitive fluorescence response was observed for CP
14
due to the higher BMA side-chain content
which is known to have stronger interaction with lysine.
关键词
聚集诱导发光增强五苯基吡咯侧基聚甲基丙烯酸酯共聚物赖氨酸荧光响应
Keywords
Aggregation-enhanced emissionPentaphenylpyrroleside groupPolymethacrylate copolymerLysine fluorescence detecting
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