Issue 33, 2012

Effect of alicyclic ring size on the photophysical and photochemical properties of bis(arylidene)cycloalkanone compounds

Abstract

A series of bis(arylidene)cycloalkanone compounds based on cyclobutanone, cyclopentanone, cyclohexanone and cycloheptanone, C4–C7, respectively, with a D-π-A-π-D structure containing the same donor and acceptor but different alicyclic rings was prepared. The effects of alicyclic ring size on the photophysical, photochemical and electrochemical properties of these compounds were investigated systematically. We found that an increase of the number of carbons in the central alicyclic ring leads to changes in geometry, which has significant effects on the conjugation, and photophysical and photochemical properties. These effects include decreases in the fluorescence quantum yield, transient lifetimes, peak extinction coefficients, and the singlet oxygen quantum yield with the increase of the ring size. The one-photon absorption spectra, the two-photon absorption (2PA) spectra, and the fluorescence spectra all show a hypsochromic shift with increasing ring size. The results of this study provide guidance for the design of new cycloketone-based D-π-A-π-D 2PA compounds for photopolymerization and photodynamic therapy applications.

Graphical abstract: Effect of alicyclic ring size on the photophysical and photochemical properties of bis(arylidene)cycloalkanone compounds

Article information

Article type
Paper
Submitted
12 Jun 2012
Accepted
29 Jun 2012
First published
25 Jul 2012

Phys. Chem. Chem. Phys., 2012,14, 11743-11752

Effect of alicyclic ring size on the photophysical and photochemical properties of bis(arylidene)cycloalkanone compounds

Q. Zou, Y. Zhao, N. S. Makarov, J. Campo, H. Yuan, D. Fang, J. W. Perry and F. Wu, Phys. Chem. Chem. Phys., 2012, 14, 11743 DOI: 10.1039/C2CP41952A

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