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Tropylium cation-fused aromatic [26]dicarbaporphyrinoids with NIR absorptions: Synthesis, spectroscopic and theoretical characterization.

Krushna Chandra, Sahoo and Sangeetha, M. and Usharani, D. and Harapriya, Rath Tropylium cation-fused aromatic [26]dicarbaporphyrinoids with NIR absorptions: Synthesis, spectroscopic and theoretical characterization. Journal of Porphyrins and Phthalocyanines, 24 (1). pp. 161-170.

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Abstract

An easy and efficient synthetic methodology for two hitherto unknown tropylium-cationfused Hückel aromatic [26] dicarbaporphyrinoids has been developed by acid-catalyzed Lindsey type condensation of bithiophene/biselenophene diol with azulene using BF3 . Et2O followed by oxidation with chloranil and/or DDQ. Both the macrocycles have been achieved in moderately good yields. Their structures, aromaticity and optical properties have been elucidated by NMR, UV-vis-NIR spectroscopic analyses and in-depth theoretical calculations. Both the macrocycles exhibited strongly diatropic characteristics with the UV-vis spectra closely resembling the spectra for true porphyrins. Detailed structural analyses using 1H–1H COSY, ROESY and DFT level theoretical investigations indicated fully conjugated [26]p main conjugation pathway being benefitted by the tropylium character of the seven membered rings.

Item Type: Article
Uncontrolled Keywords: Hückel topology, core modification, carbaporphyrinoids, aromaticity, NIR absorption, DFT calculations.
Subjects: 500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 24 Organic Chemistry
Divisions: Food Safety Analytical Quality Control Lab
Depositing User: Food Sci. & Technol. Information Services
Date Deposited: 15 Jun 2020 11:26
Last Modified: 15 Jun 2020 11:26
URI: http://ir.cftri.com/id/eprint/14397

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