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压力和酸响应的四苯乙烯修饰喹喔啉类荧光染料的合成与性质研究
  • ISSN号:0567-7351
  • 期刊名称:《化学学报》
  • 时间:0
  • 分类:O626[理学—有机化学;理学—化学]
  • 作者机构:吉林大学化学学院超分子结构与材料国家重点实验室,长春130021
  • 相关基金:国家自然科学基金(No.21374041); 超分子结构与材料国家重点实验室开放课题(No.2015014)资助
中文摘要:

合成了新的给受体型四苯乙烯修饰的喹喔啉衍生物BTPQ、DBTPQ和BTBQ.三个化合物表现出不同程度的聚集诱导发光(AIE)行为,当BTBQ(四苯乙烯单元修饰在喹喔啉的2,3-位)的四氢呋喃溶液中含水量达到90%时,其荧光发射强度增加至原来的54倍.此外,固体BTBQ在三氟乙酸蒸气作用下可由淡黄色变成红色,且其蓝绿色荧光被显著猝灭,可见,它可作为传感材料用于酸蒸气的可视化检测.由于连接在喹喔啉5,8-位上的四苯乙烯单元的空阻作用导致BTPQ和DBTPQ不易被质子化,因此,二者对酸不敏感,但是,它们的固态发光颜色在研磨前后发生了明显变化,如,BTPQ在结晶态时发射蓝色荧光,经研磨变成无定形态后,发射蓝绿色荧光,BTPQ和DBTPQ的压致荧光变色行为在研磨、加热/溶剂熏蒸处理下具有可逆性。

英文摘要:

Three new D-?-A type quinoxalines modified with tetraphenylethylenes BTPQ, DBTPQ and BTBQ were synthesized via Suzuki coupling reactions between(4-(1,2,2-triphenylvinyl)phenyl)boronic acid and bromo aromatic hydrocarbons. It was found that BTPQ and DBTPQ, in which tetraphenylethylenes were substituted on 5,8-positions of quinoxalines gave the absortion bands at 316 nm and 303 nm, respectively, originated from π-π* transition. For BTBQ, in which tetraphenylethylene units were located at 2,3-positions of quinoxaline, the π-π* transition absorption blue-shifted to 287 nm on account of the poor planarity and low conjugation. Meanwhile, the intermolecular charge transfer(ICT) emission could be detected for BTPQ and DBTPQ, whose emission bands red-shifted significantly and emission intensities decreased with increasing the solvent polarities. It should be noted that the three compounds exhibited aggregation-induced emission(AIE) behaviors. For instance, when the water faction in the THF solution increased to 90%, the emission intensity at ca. 400 nm for BTBQ, was ca. 54 times higher than that in THF. Additionally, trifluoroacetic acid(TFA) could lead to the changes of color and emitting color of BTBQ in solution as well as in solid state due to the formation of protonated quinoxaline. We found that the grey solid of BTBQ could turn into red one upon exposed to gaseous TFA, accompanying with the quench of the emission. Other kinds of acids of HCl, HNO3 and acetic acid also could lead to the fluorescence quenching of solid BTBQ to some extent. Therefore, BTBQ could be used as sensory material to detect acid vapors by naked eyes. However, the protonation would be prohibited in BTPQ and DBTPQ on account of the steric effect of tetraphenylethylene units linked to 5,8-positions of quinoxaline, so BTPQ and DBTPQ could not detect acid. Interestingly, the solid emitting colors of BTPQ as well as DBTPQ were quite different before and after grinding, exhibiting mechanochromic properties. The as-prepa

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期刊信息
  • 《化学学报》
  • 北大核心期刊(2014版)
  • 主管单位:中国科学院
  • 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:周其林
  • 地址:上海市零陵路345号
  • 邮编:200032
  • 邮箱:hxxb@sioc.ac.cn
  • 电话:021-54925085
  • 国际标准刊号:ISSN:0567-7351
  • 国内统一刊号:ISSN:31-1320/O6
  • 邮发代号:4-209
  • 获奖情况:
  • 首届国家期刊奖,第二届国家期刊奖提名奖,中国期刊方阵“双高期刊”
  • 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),英国英国皇家化学学会文摘,中国北大核心期刊(2000版)
  • 被引量:28694