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首页> 外文期刊>Chemistry: A European journal >Experimental and Theoretical Studies of Quadrupolar Oligothiophene-Cored Chromophores Containing Dimesitylboryl Moieties as p-Accepting End-Groups: Syntheses, Structures, Fluorescence, and One- and Two-Photon Absorption
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Experimental and Theoretical Studies of Quadrupolar Oligothiophene-Cored Chromophores Containing Dimesitylboryl Moieties as p-Accepting End-Groups: Syntheses, Structures, Fluorescence, and One- and Two-Photon Absorption

机译：含二甲磺酰基作为p端基的四极寡聚噻吩类发色团的实验和理论研究：合成，结构，荧光和一和两个光子吸收。

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摘要

Quadrupolar oligothiophene chromophores composed of four to five thiophene rings with two terminal (E)- dimesitylborylvinyl groups (4V-5V), and five thiophene rings with two terminal aryldimesitylboryl groups (5B), as well as an analogue of 5V with a central EDOT ring (5VE), have been synthesized via Pd-catalyzed cross-coupling reactions in high yields (66-89 %). Crystal structures of 4V, 5B, bithiophene 2V, and five thiophene-derived intermediates are reported. Chromophores 4V, 5V, 5B and 5VE have photoluminescence quantum yields of 0.26-0.29, which are higher than those of the shorter analogues 1V-3V (0.01- 0.20), and short fluorescence lifetimes (0.50-1.05 ns). Twophoton absorption (TPA) spectra have been measured for 2V-5V, 5B and 5VE in the range 750-920 nm. The measured TPA cross-sections for the series 2V-5V increase steadily with length up to a maximum of 1930 GM. We compare the TPA properties of 2V-5V with the related compounds 5B and 5VE, giving insight into the structure-property relationship for this class of chromophore. DFT and TDDFT results, including calculated TPA spectra, complement the experimental findings and contribute to their interpretation. A comparison to other related thiophene and dimesitylboryl compounds indicates that our design strategy is promising for the synthesis of efficient dyes for two-photon-excited fluorescence applications.
机译：四极低聚噻吩发色团，由四个至五个带有两个末端（E）-二甲基异丁烯基乙烯基（4V-5V）的噻吩环和五个带有两个末端芳基二甲基异丁烯基（5B）的噻吩环以及一个带有中心EDOT环的5V类似物组成（5VE），是通过Pd催化的交叉偶联反应以高收率（66-89％）合成的。报道了4V，5B，联噻吩2V和5个噻吩衍生的中间体的晶体结构。发色团4V，5V，5B和5VE的光致发光量子产率为0.26-0.29，高于较短的类似物1V-3V（0.01-0.20），并且荧光寿命短（0.50-1.05 ns）。已针对750-920 nm范围内的2V-5V，5B和5VE测量了双光子吸收（TPA）光谱。 2V-5V系列的测得的TPA横截面随着长度的增加而稳定增加，最大长度为1930 GM。我们将2V-5V的TPA特性与相关化合物5B和5VE进行了比较，从而洞察了此类生色团的结构-性质关系。 DFT和TDDFT结果（包括计算出的TPA光谱）可补充实验结果并有助于其解释。与其他相关的噻吩和二甲磺酰基化合物的比较表明，我们的设计策略对于合成用于双光子激发的荧光应用的高效染料很有希望。

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