NDLI: Versatile Photophysical Properties of meso-Aryl-Substituted Subporphyrins: Dipolar and Octupolar Charge-Transfer Interactions

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Versatile Photophysical Properties of meso-Aryl-Substituted Subporphyrins: Dipolar and Octupolar Charge-Transfer Interactions

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Versatile Photophysical Properties of meso-Aryl-Substituted Subporphyrins: Dipolar and Octupolar Charge-Transfer Interactions

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Osuka, Atsuhiro Shin, Jae-yoon Easwaramoorthi, Shanmugam Kim, Dongho Inokuma, Yasuhide Tsurumaki, Eiji Cho, Sung Kim, Pyosang
Description	Author Affiliation: Easwaramoorthi S ( Spectroscopy Laboratory for Functional pi-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749, Korea.)
Abstract	Donor–acceptor systems based on subporphyrins with nitro and amino substituents at meta and para positions of the meso-phenyl groups were synthesized and their photophysical properties have been systematically investigated. These molecules show two types of charge-transfer interactions, that is, from center to periphery and periphery to center depending on the peripheral substitution, in which the subporphyrin moiety plays a dual role as both donor and acceptor. Based on the solvent-polarity-dependent photophysical properties, we have shown that the fluorescence emission of para isomers originates from the solvatochromic, dipolar, symmetry-broken, and relaxed excited states, whereas the non-solvatochromic fluorescence of meta isomers is of the octupolar type with false symmetry breaking. The restricted meso-(4-aminophenyl) rotation at low temperature prevents the intramolecular charge-transfer (ICT)-forming process. The two-photon absorption (TPA) cross-section values were determined by photoexcitation at 800 nm in nonpolar toluene and polar acetonitrile solvents to see the effect of ICT on the TPA processes. The large enhancement in the TPA cross-section value of approximately 3200 GM $(1 GM=10^{−50} cm^{4} s photon^{−1})$ with donor–acceptor substitution has been attributed to the octupolar effect and ICT interactions. A correlation was found between the electron-donating/-withdrawing abilities of the peripheral groups and the TPA cross-section values, that is, p-aminophenyl>m-aminophenyl>nitrophenyl. The increased stability of octupolar ICT interactions in highly polar solvents enhances the TPA cross-section value by a factor of approximately 2 and 4, respectively, for p-amino- and m-nitrophenyl-substituted subporphyrins. On the other hand, the stabilization of the symmetry-broken, dipolar ICT state gives rise to a negligible impact on the TPA processes.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	44
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-11-09
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Porphyrins Chemistry Absorption Crystallography, X-Ray Electron Transport Magnetic Resonance Spectroscopy Photons Spectrometry, Fluorescence Temperature Time Factors Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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