Premium
Dipolar Dyes with a Pyrrolo[2,3‐ b ]quinoxaline Skeleton Containing a Cyano Group and a Bridged Tertiary Amino Group: Synthesis, Solvatofluorochromism, and Bioimaging
Author(s) -
Łukasiewicz Łukasz G.,
Deperasińska Irena,
Poronik Yevgen M.,
Jun Yong Woong,
Banasiewicz Marzena,
Kozankiewicz Bolesław,
Ahn Kyo Han,
Gryko Daniel T.
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600257
Subject(s) - moiety , chemistry , quinoxaline , chromophore , molecule , stereochemistry , group (periodic table) , fluorene , ring (chemistry) , crystallography , photochemistry , organic chemistry , polymer
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‐1 H ‐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.