We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Deprotonation-Induced Aromaticity Enhancement and New Conjugated Networks in meso-Hexakis(pentafluorophenyl)[26]hexaphyrin.
- Authors
Cha, Won-Young; Lim, Jong Min; Yoon, Min-Chul; Sung, Young Mo; Lee, Byung Sun; Katsumata, Sho; Suzuki, Masaaki; Mori, Hirotaka; Ikawa, Yoshiya; Furuta, Hiroyuki; Osuka, Atsuhiro; Kim, Dongho
- Abstract
meso-Hexakis(pentafluorophenyl)-substituted neutral hexaphyrin with a 26π-electronic circuit can be regarded as a real homolog of porphyrin with an 18π-electronic circuit with respect to a quite flat molecular structure and strong aromaticity. We have investigated additional aromaticity enhancement of meso-hexakis(pentafluorophenyl)[26]hexaphyrin(1.1.1.1.1.1) by deprotonation of the inner NH groups in the macrocyclic molecular cavity to try to induce further structural planarization. Deprotonated mono- and dianions of [26]hexaphyrin display sharp B-like bands, remarkably strong fluorescence, and long-lived singlet and triplet excited-states, which indicate enhanced aromaticity. Structural, spectroscopic, and computational studies have revealed that deprotonation induces structural deformations, which lead to a change in the main conjugated π-electronic circuit and cause enhanced aromaticity.
- Publication
Chemistry - A European Journal, 2012, Vol 18, Issue 49, p15838
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201200991