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

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Relation http://ir.cftri.com/14397/
https://doi.org/10.1142/S1088424619501001
 
Title Tropylium cation-fused aromatic [26]dicarbaporphyrinoids with NIR absorptions: Synthesis, spectroscopic and theoretical characterization.
 
Creator Krushna Chandra, Sahoo
Sangeetha, M.
Usharani, D.
Harapriya, Rath
 
Subject 24 Organic Chemistry
 
Description 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.
 
Date 2019
 
Type Article
PeerReviewed
 
Format pdf
 
Language en
 
Identifier http://ir.cftri.com/14397/1/Journal%20of%20Porphyrins%20and%20Phthalocyanines%202020.pdf
Krushna Chandra, Sahoo and Sangeetha, M. and Usharani, D. and Harapriya, Rath (2019) Tropylium cation-fused aromatic [26]dicarbaporphyrinoids with NIR absorptions: Synthesis, spectroscopic and theoretical characterization. Journal of Porphyrins and Phthalocyanines, 23. pp. 1-10.