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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
  • ISSN号:0253-2786
  • 期刊名称:有机化学
  • 时间:2014.3
  • 页码:537-545
  • 分类:O625.12[理学—有机化学;理学—化学]
  • 作者机构:[1]东南大学化学化工学院,南京211189
  • 相关基金:国家自然科学基金(No.61178057)资助项目.
  • 相关项目:用于生物标记及荧光成像dendrimer分子的多光子上转换荧光发射及荧光共振能量传递
作者: 管成飞|钱鹰|
中文摘要:

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1HNMR,13CNMR,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(THFl的3倍,呈现聚集荧光增强性质.在800nm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101GM.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.

英文摘要:

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 sol- vent 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.

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期刊信息
  • 《有机化学》
  • 中国科技核心期刊
  • 主管单位:
  • 主办单位:中国化学会 中国科学院上海有机化学研究所
  • 主编:陈庆云
  • 地址:上海市枫林路354号
  • 邮编:200032
  • 邮箱:bianji@mail.sioc.ac.cn
  • 电话:021-54925244
  • 国际标准刊号:ISSN:0253-2786
  • 国内统一刊号:ISSN:31-1321/O6
  • 邮发代号:4-285
  • 获奖情况:
  • 中国期刊方阵“双效”期刊
  • 国内外数据库收录:
  • 俄罗斯文摘杂志,美国化学文摘(网络版),荷兰文摘与引文数据库,美国科学引文索引(扩展库),日本日本科学技术振兴机构数据库,中国中国科技核心期刊,中国北大核心期刊(2004版),中国北大核心期刊(2008版),中国北大核心期刊(2011版),中国北大核心期刊(2014版),中国北大核心期刊(2000版)
  • 被引量:14408