title: Benzo[1,2-d:4,5-d']bisimidazoles as a convenient platform towards dyes that are capable of excited-state intramolecular proton transfer and of two-photon absorption.
abstract: New, strongly fluorescent benzo[1,2-d:4,5-d']bisimidazoles have been prepared by the reaction of Bandrowski's base with various aldehydes. Their structures were carefully designed to achieve efficient excited-state intramolecular proton transfer and good two-photon-absorption (2PA) cross-sections. Functional dyes that possessed both high fluorescence quantum yields and large Stokes shifts were prepared. A π-expanded D-A-D derivative that possessed Φ(fl)=50 % and σ(2)=230 GM in the spectroscopic area of interest for biological imaging is an excellent candidate as a fluorescent probe. Thanks to the presence of two reactive amino groups, such compounds can be easily transformed into probes for bioconjugation. All of these benzo[1,2-d:4,5-d']bisimidazoles were also strongly fluorescent in the solid state.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Mariusz
authors.initials: M
authors.lastname: Tasior
authors.forename: Vincent
authors.initials: V
authors.lastname: Hugues
authors.forename: Mireille
authors.initials: M
authors.lastname: Blanchard-Desce
authors.forename: Daniel T
authors.initials: DT
authors.lastname: Gryko
mesh_terms: D000042:Absorption; D000447:Aldehydes / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D017785:Photons; D011522:Protons; D011789:Quantum Theory
chemical_list: D000447:Aldehydes; D005456:Fluorescent Dyes; D007093:Imidazoles; D011522:Protons