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

doi:10.6023/cjoc201309005

摘要/Abstract

通过Heck反应合成了2个以吡啶为端基的9，10-双芳基蒽共轭分子9，10-二{4-{4-[N，N-二（4-吡啶乙烯基）苯基]氨基}苯乙烯基}蒽（4Py-PAA）和9，10-二{4-{4-[N，N-二（2-吡啶乙烯基）苯基]氨基}苯乙烯基}蒽（2Py-PAA），化合物结构经过¹H NMR，¹³C NMR，HRMS-MALDI-TOF确证. 测定了化合物在不同极性溶剂中的紫外吸收光谱、荧光光谱、荧光寿命及量子产率，测算了4Py-PAA和2Py-PAA的偶极矩. 通过循环伏安法研究了它们的前线轨道能级. 测定了4Py-PAA和2Py-PAA的固体荧光光谱、固体荧光量子产率及在不同含水量的水/THF混合溶液中的荧光光谱. 实验发现4Py-PAA在THF溶液中发出蓝绿色荧光，固体时发出红色荧光，在含水量为70%的水/THF混合溶剂中发出黄色荧光，荧光强度是纯四氢呋喃（THF）的3倍，呈现聚集荧光增强性质. 在800 nm飞秒激光下采用双光子诱导荧光参比法测定了4Py-PAA和2Py-PAA在THF溶液中的双光子吸收截面分别为193和101 GM. 实验结果表明含有2位和4位吡啶端基9，10-双芳基蒽共轭分子具有良好的荧光发射性能及双光子吸收性质.

关键词: Heck反应, 吡啶取代基, 9,10-双芳基蒽, 聚集荧光增强, 溶剂效应, 双光子诱导荧光

New dendrimers 9,10-bis{4-[N,N-bis(4-pyridylvinyl)phenylamino]styryl}anthracene (4Py-PAA) and 9,10-bis{4-[N,N-bis(2-pyridylvinyl)phenylamino]styryl}anthracene (2Py-PAA) were synthesized by Heck coupling reaction with pyridine as branches, and anthracene as the core. The structures were characterized by ¹H NMR, ¹³C NMR, HRMS-MALDI-TOF. The UV-vis spectra, fluorescence spectra, fluorescence lifetime and quantum yields were measured, and dipole moments of 4Py-PAA and 2Py-PAA were calculated. The frontier orbitals were studied by cyclic voltammetry. Solid fluorescence spectra, fluorescence spectra in aqueous tetrahydrofuran (THF) with different water/THF ratios and absolute quantum yield of 4Py-PAA and 2Py-PAA were measured. 4Py-PAA emitted blue-green light in THF and red light in the solid state. In the solvent mixture with 70% water, 4Py-PAA emitted a yellow light and the intensity was 3-fold higher than that in THF. Therefore, 4Py-PAA is AIEE-active. Measured with the two-photon induced fluorescence method, the values of TPA cross-section of 4Py-PAA and 2Py-PAA in THF were 193 and 101 GM, which obtained at 800 nm wavelength from a femtosecond laser source. The results showed that 9,10-diaryl anthracene end-capped with 2-pyridine and 4-pyridine had good fluorescence and two-photon absorption properties.

Key words: Heck reaction, pyridine substituent, 9,10-diaryl anthracene, aggregation-induced emission enhancement, solvatochromic behavior, two-photon induced fluorescence

引用此文

管成飞, 钱鹰. 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[J]. 有机化学, 2014, 34(3): 537-545.

Guan Chengfei, Qian Ying. Synthesis, Aggregation-Induced Emission Enhancement and Two-Photon Induced Fluorescence of Pyridine End-Capped 9,10-Diaryl Anthracene[J]. Chin. J. Org. Chem., 2014, 34(3): 537-545.

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