Theoretical study on conformation and electronic state of Hückel-aromatic multiply N-confused [26]hexaphyrins

Motoki Toganoh, Hiroyuki Furuta

    研究成果: ジャーナルへの寄稿学術誌査読

    29 被引用数 (Scopus)

    抄録

    Conformations and electronic states of Hückel-aromatic regular, singly, doubly, and triply N-confused [26]hexaphyrins were investigated using density functional theory (DFT) calculations. A comparison of the molecular energies of 754 structures in all revealed that the most stable conformers depend on the degree of confusion, where ring strain and intramolecular hydrogen bonding would play a critical role. Consequently, regular and singly N-confused hexaphyrins prefer a dumbbell conformation, doubly N-confused hexaphyrin prefers a rectangular conformation, and triply N-confused hexaphyrin prefers a triangular conformation. Introduction of N-confused pyrrole rings into the hexaphyrin framework causes narrower HOMO-LUMO energy gaps, while it does not affect the NICS values or aromaticity significantly. The steric repulsion imposed by meso-aryl substituents largely affects the relative energies among the conformers.

    本文言語英語
    ページ(範囲)8213-8223
    ページ数11
    ジャーナルJournal of Organic Chemistry
    75
    23
    DOI
    出版ステータス出版済み - 12月 3 2010

    !!!All Science Journal Classification (ASJC) codes

    • 有機化学

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