Dipolar Dyes with a Pyrrolo[2,3-b]quinoxaline Skeleton Containing a Cyano Group and a Bridged Tertiary Amino Group: Synthesis, Solvatofluorochromism, and Bioimaging

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 pyrrolo[2,3‐b]quinoxaline ring system. The photophysical proper...

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Published in:Chemistry, an Asian journal an Asian journal, 2016-06, Vol.11 (11), p.1718-1724
Main Authors: Łukasiewicz, Łukasz G., Deperasińska, Irena, Poronik, Yevgen M., Jun, Yong Woong, Banasiewicz, Marzena, Kozankiewicz, Bolesław, Ahn, Kyo Han, Gryko, Daniel T.
Format: Article
Language:English
Subjects:
Animals
Cervical Vertebrae - diagnostic imaging
Chemistry
Crystallography, X-Ray
dyes/pigments
fluorescence
Fluorescent Dyes - chemistry
fused-ring systems
heterocycles
Mice
Molecular Conformation
photophysics
Quantum Theory
Quinoxalines - chemical synthesis
Quinoxalines - chemistry
Solvents - chemistry
Spectrometry, Fluorescence
Stereoisomerism
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Summary: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 pyrrolo[2,3‐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‐tetraazabenzo[b]cyclohepta[1,2,3‐jk]fluorene, was successfully utilized in two‐photon imaging of mouse organ tissues and showed distinct tissue morphology with high resolution. Exciting dyes: The addition of a cyano group to a 2‐aminopyrrolo[2,3‐b]quinoxaline core results in strong solvatofluorochromism. Internal charge transfer combined with a bridged tertiary amino group are responsible for a very high fluorescence quantum yield in nonpolar solvents. Optical properties make it possible to achieve high‐resolution imaging of mouse tissues by using two‐photon excitation.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201600257