Synthesis, Aggregation-Induced Emission Enhancement and Two-Photon Induced Fluorescence of Pyridine End-Capped 9,10-Diaryl Anthracene

doi:10.6023/cjoc201309005

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (3): 537-545.DOI: 10.6023/cjoc201309005 Previous Articles Next Articles

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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

管成飞, 钱鹰

东南大学化学化工学院南京 211189

收稿日期:2013-09-03 修回日期:2013-10-27 发布日期:2013-11-20
通讯作者: 钱鹰 E-mail:yingqian@seu.edu.cn
基金资助:
国家自然科学基金（No. 61178057）资助项目.

Synthesis, Aggregation-Induced Emission Enhancement and Two-Photon Induced Fluorescence of Pyridine End-Capped 9,10-Diaryl Anthracene

Guan Chengfei, Qian Ying

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Received:2013-09-03 Revised:2013-10-27 Published:2013-11-20
Supported by:
Project supported by the National Natural Science Foundation of China (No. 61178057).

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

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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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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

Synthesis, Aggregation-Induced Emission Enhancement and Two-Photon Induced Fluorescence of Pyridine End-Capped 9,10-Diaryl Anthracene

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