Please use this identifier to cite or link to this item: https://doi.org/10.1002/anie.202000188
Title: Porphyrin/Quinoidal Bithiophene Based Macrocycles and Their Dications: Template-free Synthesis and Global Aromaticity
Authors: REN LONGBIN 
YADAGIRI GOPALAKRISHNA TULLIMILLI 
PARK IN-HYEOK 
Han, Y.
Wu Jishan 
Issue Date: 6-Nov-2010
Publisher: Wiley-VCH Verlag
Citation: REN LONGBIN, YADAGIRI GOPALAKRISHNA TULLIMILLI, PARK IN-HYEOK, Han, Y., Wu Jishan (2010-11-06). Porphyrin/Quinoidal Bithiophene Based Macrocycles and Their Dications: Template-free Synthesis and Global Aromaticity. Angewandte Chemie International Edition 59 (6) : 2230-2234. ScholarBank@NUS Repository. https://doi.org/10.1002/anie.202000188
Abstract: We report the template-free synthesis and characterization of a new type of porphyrin/quinoidal-bithiophene-based conjugated macrocycle. X-ray crystallographic analysis of the dimer (2MC) revealed a cyclophane-like geometry with large dihedral angles between the porphyrin and the neighboring thiophene rings, and NMR measurements and theoretical calculations confirmed a localized aromatic character of the porphyrin/thiophene rings and quinoidal character of the bithiophene linkers. Restricted rotation of the thiophene rings linked to the porphyrin unit was observed by variable-temperature NMR measurements. The dication (2MC2+) adopts a chair-shaped conformation to facilitate π-electron delocalization around the whole macrocycle. As a result, the molecule is globally aromatic, with a dominant 54 π conjugation pathway. The trimer (3MC) also shows localized aromatic character of porphyrin rings and conformational flexibility, but its dication (3MC2+) is rigid and globally aromatic with a dominant 82 π conjugation pathway.
Source Title: Angewandte Chemie International Edition
URI: https://scholarbank.nus.edu.sg/handle/10635/167841
ISSN: 1433-7851
1521-3773
DOI: 10.1002/anie.202000188
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