Dibenzoborole-Containing π-Electron Systems: Remarkable Fluorescence Change Based on the “On/Off” Control of the pπ−π* Conjugation
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- 1 July 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (30) , 8816-8817
- https://doi.org/10.1021/ja026689k
Abstract
A series of dibenzoborole derivatives with various groups such as (N,N-diphenylamino)phenyl, thienyl, and bithienyl groups at the 3,7-positions have been synthesized and their photophysical properties studied. These new π-electron systems show significant solvatochromism in the fluorescence spectra. Thus, about 100−140 nm blue shifts in the emission maxima and 20−30-fold increments in the quantum yields are observed upon changing the solvent from THF to DMF. Similar fluorescence changes are observed upon the addition of n-Bu4NF to their THF solutions, demonstrating their sensing abilities toward a fluoride ion. These fluorescence changes result from the “on/off” control of the pπ−π* conjugation in their LUMO by the coordination of donor solvents or fluoride ion to the boron atom in the dibenzoborole skeleton.Keywords
This publication has 23 references indexed in Scilit:
- New Fluorinated 9-Borafluorene Lewis AcidsJournal of the American Chemical Society, 2000
- 4-Boratastyrylstilbene and 1,4-Bis(boratastyryl)benzene: Synthesis, Structural Characterization, and PhotophysicsJournal of the American Chemical Society, 2000
- Tri-9-anthrylborane and Its Derivatives: New Boron-Containing π-Electron Systems with Divergently Extended π-Conjugation through BoronJournal of the American Chemical Society, 2000
- Poly(p-phenylene-borane)s. Novel Organoboron π-Conjugated Polymers via Grignard ReagentJournal of the American Chemical Society, 1998
- Extension of π-Conjugation Length via the Vacant p-Orbital of the Boron Atom. Synthesis of Novel Electron Deficient π-Conjugated Systems by Hydroboration Polymerization and Their Blue Light EmissionJournal of the American Chemical Society, 1998
- 1-Phenylthieno[3,4-d]borepin: a new 10 .pi. electron system isoelectronic with azuleneJournal of the American Chemical Society, 1992
- An ab initio study of potentially aromatic and antiaromatic three-membered ringsJournal of the American Chemical Society, 1991
- Bora-aromatic systems. Part 10. Aromatic stabilization of the triarylborirene ring system by tricoordinate boron and facile ring-opening with tetracoordinate boronJournal of the American Chemical Society, 1990
- Organic quantum chemistry. XXXIII. Electronic spectra and rotational barriers of vinylborane, allyl cation, and related compoundsJournal of the American Chemical Society, 1975
- Borverbindungen, XI. Pyrolyseprodukte einiger Aralkyl- und ArylboraneEuropean Journal of Organic Chemistry, 1967