Donor-and-acceptor substituted truxenes as multifunctional fluorescent probes.
Donor-and-acceptor substituted truxenes as multifunctional fluorescent probes.
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DOI：
10.1021/jo071064w
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发表时间：
2007-09
期刊：
影响因子：
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通讯作者：
Mao-Sen Yuan;Zhi-qiang Liu;Q. Fang
中科院分区：
文献类型：
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作者：
Mao-Sen Yuan;Zhi-qiang Liu;Q. Fang
合成了一系列二均三甲苯基硼基受体（均三甲苯基= 2，4，6-三甲基苯基）和/或二苯胺基给体（-N（Ph）2）取代的三聚氧乙烯衍生物，分为D-或A-取代化合物和D-和A-取代电荷转移化合物。两个D-和A-取代的truxene化合物，即2-dimesitylboryl-7，12-di（N，N-二苯氨基）-5，5 '，10，10'，15，15 '-六乙基三苯醚（BN 2）和2，7-二（二均三甲苯硼基）-12-（N，N-二苯基氨基）-5，5 '，10，10'，15，15 '-六乙基三苯（B2 N），在非质子溶剂中表现出从420 nm（在己烷中）到580 nm（在乙腈中）范围内的非常大的溶致变色，这可用于探测溶液环境的极性。由于质子-给体相互作用，BN 2和B2 N在质子溶剂中的溶致变色红移显著降低，这种效应可用于识别局部质子和非质子环境。此外，由于F-和受体之间的相互作用，BN 2和B2 N对氟离子浓度表现出尖锐的光谱响应。荧光信号在500 nm处的同时“关闭”和在380 nm处的“开启”提供了荧光比率法的一个很好的例子，这可以大大提高氟离子探针的灵敏度。在这些有趣的光谱现象和多功能探针性质的基础上，是将供体和受体部分（如A-pi-D2或A2-pi-D样式）接枝到三角形truxene的电荷转移策略。
A series of dimesitylboryl acceptor (mesityl=2,4,6-trimethylphenyl) and/or diphenylamino donor (-N(Ph)2)-substituted truxene derivatives, classified as D-or-A substituted compounds and D-and-A substituted charge-transfer compounds, have been synthesized. Two D-and-A substituted truxene compounds, namely, 2-dimesitylboryl-7,12-di(N,N-diphenylamino)-5,5',10,10',15,15'-hexaethyltruxene (BN2) and 2,7-di(dimesitylboryl)-12-(N,N-diphenylamino)-5,5',10,10',15,15'-hexaethyltruxene (B2N), exhibit extraordinarily large solvatochromism ranging from 420 nm (in hexane) to 580 nm (in acetonitrile) in aprotic solvents, which can be used to probe the polarity of the solution environment. Due to proton-donor interactions, the solvatochromic red shift of BN2 and B2N in protic solvents has been significantly decreased, and this effect can be used to identify local protic and aprotic environment. Furthermore, because of the interaction between F- and acceptor, BN2 and B2N show sharp spectral response to fluoride ion concentration. The simultaneous "turn-off" at 500 nm and "turn-on" at 380 nm of the fluorescence signal have provided a good example of a fluorescent ratiometric method, which can greatly enhance the sensitivity of the fluoride ion probe. Underlying these interesting spectral phenomena and multifunctional probe properties is the charge-transfer strategy of grafting donor and acceptor moieties, as A-pi-D2 or A2-pi-D style, to the triangular truxene.