Please use this identifier to cite or link to this item: https://doi.org/10.1021/ja0382260
Title: Evidence for Homo-Conjugation between Two Revolving 14π-Electron Systems in 10b-Methyl-10c-[2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)]-10b, 10c-dihydropyrene
Authors: Jiang, J.
Lai, Y.-H. 
Issue Date: 26-Nov-2003
Citation: Jiang, J., Lai, Y.-H. (2003-11-26). Evidence for Homo-Conjugation between Two Revolving 14π-Electron Systems in 10b-Methyl-10c-[2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)]-10b, 10c-dihydropyrene. Journal of the American Chemical Society 125 (47) : 14296-14297. ScholarBank@NUS Repository. https://doi.org/10.1021/ja0382260
Abstract: Ring contraction followed by an elimination reaction on anti-9-methyl-18-trans-2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)-2,11-dithia[3,3]metacyclophane gave the desired compound 10b-methyl-10c-[2-(10b,10c-dimethyl-10b,10c-dihydropyrenyl)]-10b,10c-dihydropyrene. 1H NMR spectroscopic analysis indicated a ring current effect over a considerable distance from the macro-molecular plane of each of the aromatic rings with the two π systems freely rotating. Bathochromic shifts and peak broadening in its electronic spectrum clearly supports the presence of through-space π?π interactions between the two aromatic rings. This should serve as a good model to verify homo-conjugation effect in such a novel system where the two π systems are freely revolving. Copyright © 2003 American Chemical Society.
Source Title: Journal of the American Chemical Society
URI: http://scholarbank.nus.edu.sg/handle/10635/93778
ISSN: 00027863
DOI: 10.1021/ja0382260
Appears in Collections:Staff Publications

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