NDLI: Flexible Tuning of Unsaturated β-Substituents on Zn Porphyrins: A Synthetic, Spectroscopic and Computational Study

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Flexible Tuning of Unsaturated β-Substituents on Zn Porphyrins: A Synthetic, Spectroscopic and Computational Study

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Van Der Salm, Holly Wagner, Pawel Officer, David L. Gordon, Keith C. Wallace, Gordon G. Wagner, Klaudia
Description	Author Affiliation: van der Salm H ( Department of Chemistry, University of Otago, Union Place, 9016 Dunedin (New Zealand).); Wagner P ( Intelligent Polymer Research Institute, University of Wollongong, Wollongong 2522 NSW (Australia). pawel@uow.edu.au.); Wagner K ( Intelligent Polymer Research Institute, University of Wollongong, Wollongong 2522 NSW (Australia).); Officer DL ( Intelligent Polymer Research Institute, University of Wollongong, Wollongong 2522 NSW (Australia).); Wallace GG ( Intelligent Polymer Research Institute, University of Wollongong, Wollongong 2522 NSW (Australia).); Gordon KC ( Department of Chemistry, University of Otago, Union Place, 9016 Dunedin (New Zealand). keith.gordon@otago.ac.nz.)
Abstract	A series of zinc porphyrins substituted at adjacent β-positions with a CN group and para-substituted ethenyl/ethynyl-phenyl group have been studied using electronic absorption spectroscopy, resonance Raman spectroscopy and DFT calculations. The oxidative nucleophilic substitution of hydrogen was utilized for the introduction of a cyano substituent on the porphyrin ring. This modification has a remarkable electronic effect on the ring. The resulting porphyrin cyanoaldehyde was further modified in Wittig condensations to give series of arylalkene- and arylalkyne-substituted derivatives. This substitution pattern caused significant redshifting and broadening of the B band, tuning from 433–446 nm. Additionally the Q/B band intensity ratios show much higher values than observed for the parent porphyrin ZnTPP (0.20 vs. 0.03). Careful analysis of the electronic transitions using DFT and resonance Raman spectroscopy reveal that the substituent does not significantly perturb the electronic structure of the porphyrin core, which is still well described by Gouterman’s four-orbital model. However, the substituents do play a role in elongating the conjugation length and this results in the observed spectral changes.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	44
Volume Number	21
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2015-10-26
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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