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

Abstract

Abstract 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. 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).

Authors:
 [1];  [1];  [1];  [1];  [1];  [1];  [1]; ORCiD logo [1]
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  1. Department of Chemistry University of North Texas 1155 Union Circle, #305070 Denton TX 76203 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1786076
Grant/Contract Number:  
SC0016766
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition) Journal Volume: 59 Journal Issue: 45; Journal ID: ISSN 1433-7851
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Hu, Yi, Thomas, Michael B., Webre, Whitney A., Moss, Austen, Jinadasa, R. G. Waruna, Nesterov, Vladimir N., D'Souza, Francis, and Wang, Hong. Nickel(II) Bisporphyrin‐Fused Pentacenes Exhibiting Abnormal High Stability. Germany: N. p., 2020. Web. doi:10.1002/anie.202008076.
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Hu, Yi, Thomas, Michael B., Webre, Whitney A., Moss, Austen, Jinadasa, R. G. Waruna, Nesterov, Vladimir N., D'Souza, Francis, & Wang, Hong. Nickel(II) Bisporphyrin‐Fused Pentacenes Exhibiting Abnormal High Stability. Germany. https://doi.org/10.1002/anie.202008076
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Hu, Yi, Thomas, Michael B., Webre, Whitney A., Moss, Austen, Jinadasa, R. G. Waruna, Nesterov, Vladimir N., D'Souza, Francis, and Wang, Hong. Mon . "Nickel(II) Bisporphyrin‐Fused Pentacenes Exhibiting Abnormal High Stability". Germany. https://doi.org/10.1002/anie.202008076.
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@article{osti_1786076,
title = {Nickel(II) Bisporphyrin‐Fused Pentacenes Exhibiting Abnormal High Stability},
author = {Hu, Yi and Thomas, Michael B. and Webre, Whitney A. and Moss, Austen and Jinadasa, R. G. Waruna and Nesterov, Vladimir N. and D'Souza, Francis and Wang, Hong},
abstractNote = {Abstract 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. 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).},
doi = {10.1002/anie.202008076},
journal = {Angewandte Chemie (International Edition)},
number = 45,
volume = 59,
place = {Germany},
year = {Mon Nov 02 00:00:00 EST 2020},
month = {Mon Nov 02 00:00:00 EST 2020}
}
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https://doi.org/10.1002/anie.202008076
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