Twisted-Planar-Twisted expanded porphyrinoid dimer as a rudimentary reaction-based methanol indicator

Qizhao Li, Chengjie Li, Glib Baryshnikov, Yubin Ding, Chengxi Zhao, Tingting Gu, Feng Sha, Xu Liang, Weihua Zhu, Xinyan Wu, Hans Ågren, Jonathan L. Sessler () and Yongshu Xie ()
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Qizhao Li: East China University of Science & Technology
Chengjie Li: East China University of Science & Technology
Glib Baryshnikov: KTH Royal Institute of Technology
Yubin Ding: East China University of Science & Technology
Chengxi Zhao: East China University of Science & Technology
Tingting Gu: Jiangsu University
Feng Sha: East China University of Science & Technology
Xu Liang: Jiangsu University
Weihua Zhu: Jiangsu University
Xinyan Wu: East China University of Science & Technology
Hans Ågren: KTH Royal Institute of Technology
Jonathan L. Sessler: The University of Texas at Austin
Yongshu Xie: East China University of Science & Technology

Nature Communications, 2020, vol. 11, issue 1, 1-11

Abstract: Abstract Directly linked porphyrin dimers have attracted considerable attention because of their intriguing electronic features. Most emphasis has been placed on either dimers with large dihedral angles between the constituent planar monomeric subunits or those with overall planarity, referred to as “Planar-Twisted-Planar” and “Planar-Planar-Planar”, respectively. Herein, we report a “Twisted-Planar-Twisted” framework, the hexaphyrin dimer D that exists in a trans configuration. Treatment of D with MeOH affords two isomeric dimers, MD1 and MD2, both of which incorporate a methoxy moiety and exist in cis orientations with respect to the tethering linkage. The methanol-promoted conversion is accompanied by a readily discernible color change from green to brown and is not induced to an appreciable level by other alcohols. Dimer D thus acts as a rudimentary, albeit highly selective, reaction-based methanol indicator. This work provides a promising approach for constructing reaction-based chemosensors using porphyrinoid dimers of nonplanar subunits with biased reactivity.

Date: 2020
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DOI: 10.1038/s41467-020-19118-9

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