Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/167847
Title: A Stable All‐thiophene‐based Core‐modified [38]Octaphyrin Diradicaloid: Conformation and Aromaticity Switch at Different Oxidation States
Authors: NI YONG 
YADAGIRI GOPALAKRISHNA TULLIMILLI 
Wu, S.
Wu Jishan 
Issue Date: 13-Feb-2020
Publisher: Wiley-VCH
Citation: NI YONG, YADAGIRI GOPALAKRISHNA TULLIMILLI, Wu, S., Wu Jishan (2020-02-13). A Stable All‐thiophene‐based Core‐modified [38]Octaphyrin Diradicaloid: Conformation and Aromaticity Switch at Different Oxidation States. Angewandte Chemie International Edition 59 (19) : 7414-7418. ScholarBank@NUS Repository.
Abstract: A soluble and stable core-modified [38]octaphyrin, MC-T8, containing eight thiophene rings was synthesized by Yamamoto coupling followed by oxidative dehydrogenation. X-ray crystallographic analysis revealed a nearly planar backbone, and the molecule is globally aromatic with a dominant 38π conjugation pathway. The dication MC-T82+ is antiaromatic, and the backbone is distorted, with a different orientation of the thiophene rings. The tetracation MC-T84+ becomes aromatic again, with a shallow-bowl-shaped geometry. Both the neutral compound and the dication demonstrated open-shell diradical character with a small singlet–triplet energy gap (−2.70 kcal mol−1 for MC-T8 and −3.78 kcal mol−1 for MC-T82+), and they are stable owing to effective spin delocalization.
Source Title: Angewandte Chemie International Edition
URI: https://scholarbank.nus.edu.sg/handle/10635/167847
ISSN: 1433-7851
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