Dipolar Dyes with a Pyrrolo[2,3‐b]quinoxaline Skeleton Containing a Cyano Group and a Bridged Tertiary Amino Group: Synthesis,Solvatofluorochromism, and Bioimaging |
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| Authors: | Łukasz G Łukasiewicz Dr Irena Deperasińska Dr Yevgen M Poronik Yong Woong Jun Dr Marzena Banasiewicz Prof Bolesław Kozankiewicz Prof Kyo Han Ahn Prof Daniel T Gryko |
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| Institution: | 1. Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland;2. Institute of Physics, Polish Academy of Sciences, Warsaw, Poland;3. Department of Chemistry, POSTECH, Pohang, Gyungbuk, Korea |
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| Abstract: | Two strongly polarized dipolar chromophores possessing a cyclic tertiary amino group at one terminus of the molecule and a CN group at the opposite terminus were designed and synthesized. Their rigid skeleton contains the rarely studied pyrrolo2,3‐b]quinoxaline ring system. The photophysical properties of these regioisomeric dyes were different owing to differing π conjugation between the CN group and the electron‐donor moiety. These dipolar molecules showed very intense emission, strong solvatofluorochromism, and sufficient two‐photon brightness for bioimaging. One of these regioisomeric dyes, namely, 11‐carbonitrile‐2,3,4,5,6,7‐hexahydro‐1H‐3a,8,13,13b‐tetraazabenzob]cyclohepta1,2,3‐jk]fluorene, was successfully utilized in two‐photon imaging of mouse organ tissues and showed distinct tissue morphology with high resolution. |
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| Keywords: | dyes/pigments fluorescence fused-ring systems heterocycles photophysics |
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