Nickel(II) Bisporphyrin‐Fused Pentacenes Exhibiting Abnormal High Stability

Journal Article · 27 July 2020 · Angewandte Chemie International Edition

DOI: https://doi.org/10.1002/anie.202008076 · OSTI ID:2589720

Hu, Yi ^[1]; Thomas, Michael B. ^[1]; Webre, Whitney A. ^[1]; Moss, Austen ^[1]; Jinadasa, R. G. Waruna ^[1]; Nesterov, Vladimir N. ^[1]; D’Souza, Francis ^[1]; Wang, Hong  ^[1]

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1. University of North Texas, Denton, TX (United States)

A series of largely π-extended multichromophoric molecules including cross-conjugated, half cross-conjugated, conjugation-interrupted and linearly conjugated systems were synthesized and characterized. These multichromophoric molecular systems revealed interesting structural-property relationships. Bisporphyrin-fused pentacenes Pen-1 b and Pen-2 a showed rich redox chemistry with 7 and 8 observable redox states, respectively. The linearly-conjugated bisporphyrin-fused pentacenes (Pen-1 b and Pen-2 a) possess much narrower HOMO–LUMO gaps (1.65 and 1.42 eV redox, respectively) and higher HOMO energy levels than those of their pentacene analogues (2.23 and 2.01 eV redox, respectively), similar to those of much less stable hexacenes and heptacenes. Here, an estimated half-life of >945 h was obtained for bisporphyrin-fused pentacene Pen-2 a, which is much longer than that of its pentacene analogue (BPE-P, half-life, 33 h).

• Research Organization: University of North Texas, Denton, TX (United States)
• Sponsoring Organization: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES)
• Grant/Contract Number: SC0016766
• OSTI ID: 2589720
• Journal Information: Angewandte Chemie International Edition, Journal Name: Angewandte Chemie International Edition Journal Issue: 45 Vol. 59; ISSN 1521-3773; ISSN 1433-7851
• Publisher: WileyCopyright Statement
• Country of Publication: United States
• Language: English