title: Dipolar Dyes with a Pyrrolo[2,3-b]quinoxaline Skeleton Containing a Cyano Group and a Bridged Tertiary Amino Group: Synthesis, Solvatofluorochromism, and Bioimaging.
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 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.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
authors.forename: Łukasz G
authors.initials: ŁG
authors.lastname: Łukasiewicz
authors.affiliation: Institute of Physics, Polish Academy of Sciences, Al. Lotników 32/46, 02-668, Warsaw, Poland.
authors.forename: Irena
authors.initials: I
authors.lastname: Deperasińska
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
authors.forename: Yevgen M
authors.initials: YM
authors.lastname: Poronik
authors.affiliation: Department of Chemistry, POSTECH, 77 Cheongam-Ro, Nam-Gu, Pohang, Gyungbuk, 37673, Korea.
authors.forename: Yong Woong
authors.initials: YW
authors.lastname: Jun
authors.affiliation: Institute of Physics, Polish Academy of Sciences, Al. Lotników 32/46, 02-668, Warsaw, Poland.
authors.forename: Marzena
authors.initials: M
authors.lastname: Banasiewicz
authors.affiliation: Institute of Physics, Polish Academy of Sciences, Al. Lotników 32/46, 02-668, Warsaw, Poland. kozank@ifpan.edu.pl.
authors.forename: Bolesław
authors.initials: B
authors.lastname: Kozankiewicz
authors.affiliation: Department of Chemistry, POSTECH, 77 Cheongam-Ro, Nam-Gu, Pohang, Gyungbuk, 37673, Korea.
authors.forename: Kyo Han
authors.initials: KH
authors.lastname: Ahn
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland. dtgryko@icho.edu.pl.
authors.forename: Daniel T
authors.initials: DT
authors.lastname: Gryko
mesh_terms: D000818:Animals; D002574:Cervical Vertebrae / Q000000981:diagnostic imaging; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000737:chemistry*; D051379:Mice; D008968:Molecular Conformation; D011789:Quantum Theory; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism
chemical_list: D005456:Fluorescent Dyes; D011810:Quinoxalines; D012997:Solvents; C000608165:pyrrolo(2,3-b)quinoxaline
keywords: dyes/pigments; fluorescence; fused-ring systems; heterocycles; photophysics