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Origin of the strong effect of protic solvents on the emission spectra, quantum yield of fluorescence and fluorescence lifetime of 4-aminophthalimide: Role of hydrogen bonds in deactivation of S1-4-aminophthalimide

Paper ID Volume ID Publish Year Pages File Format Full-Text
28465 44076 2006 15 PDF Available
Title
Origin of the strong effect of protic solvents on the emission spectra, quantum yield of fluorescence and fluorescence lifetime of 4-aminophthalimide: Role of hydrogen bonds in deactivation of S1-4-aminophthalimide
Abstract

The paper presents results of the spectral (absorption and emission) and photophysical study of 4-aminophthalimide (4-AP) in 1-chloro-n-alkanes (RCl) with which 4-AP interacts only nonspecifically, in hexafluoroisopropanol (HFIP) and dimethyl sulfoxide (DMSO) in which 4-AP forms only one type of hydrogen bond, and in water and deuterated water in which 4-AP forms both accepting and donating hydrogen bonds. Based on our solvatochromic data and independent literature data used for the determination of the energy of hydrogen bonds in the S0 state, the energies of hydrogen bonds in the S1-LE and S1-ICT states of 4-AP were estimated. The results confirmed that, apart from 4-AP, there can be S1-exciplexes (S1-exc) formed as a result of strong hydrogen-bond formation between 4-AP molecules in the S1-ICT state and the solvent molecules. In strongly protic solvents (e.g. HFIP) there can also be S0-complexes (S0-comp) in the ground state. The existence of solvent-dependent species of different character in the excited state forms the basis for explaining the origin of the large effects of protic solvents on the emission spectra, quantum yield of fluorescence, and fluorescence lifetime of 4-AP.

Keywords
4-Aminophthalimide; Exciplex; Fluorescence; Solvatochromism; Hydrogen bond
First Page Preview
Origin of the strong effect of protic solvents on the emission spectra, quantum yield of fluorescence and fluorescence lifetime of 4-aminophthalimide: Role of hydrogen bonds in deactivation of S1-4-aminophthalimide
Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 184, Issue 3, 15 December 2006, Pages 250–264
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering