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Published on: June 29, 2014
The limited extent of the electronic modulation of chlorins and bacteriochlorins through chromene-annulation
Bowen Yang1, Nisansala Hewage, Matthew J Guberman-Pfeffer
1Department of Civil and Environmental Engineering, University of Connecticut, Storrs, Connecticut 06269-3037, USA. agrios@uconn.edu.
Abstract:
Optical data (UV-vis absorption and fluorescence emission spectra, including fluorescence yields and lifetimes) and electrochemical measurements are used to quantify the modulation of the electronic properties of meso-tetrakis(pentafluorophenyl)-chlorin diol and -bacteriochlorin tetraols upon intramolecular chromene-annulation, including the investigation of regio- and stereoisomers. The small modulations of the frontier orbitals of the porphyrinoids are rationalized using DFT computations and can be traced to small electronic effects due to the co-planarized meso-aryl groups in combination with conformational effects.
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