An Unsymmetrical 5,15-Disubstituted Tetrabenzoporphyrin: Effect of Molecular Symmetry on the Packing Structure and Charge Transporting Property

Miyazaki, Kazuya, Matsuo, Kyohei, Hayashi, Hironobu, Yamauchi, Mitsuaki, Aratani, Naoki, Yamada, Hiroko

Abstract

Molecular design strategy to control the crystal structure of two-dimensional (2D) 𝝅-extended organic semiconductors has not been intensively explored. We synthesized an unsymmetric tetrabenzoporphyrin derivative (TIPS-Ph-BP) to demonstrate the effect of molecular symmetry on crystal packing. TIPS-Ph-BP formed an antiparallel slipped 𝝅-stacking and 2D herringbone-like structure. An unsymmetric structure would make 2D 𝝅-stacking more stable than a one-dimensional (1D) columnar structure to counteract steric and electronic imbalance in the crystal. As a result, TIPS-Ph-BP achieved the high hole mobility of 0.71 ㎝² V⁻¹ s⁻¹.

Journal

Organic Letters

Organic Letters 25 (40), 7354-7358, 2023-10-13

American Chemical Society (ACS)

Keywords

Details 詳細情報について

CRID: 1050579444484324864

ISSN: 15237052; 15237060

HANDLE: 2433/285766

Text Lang: en

Article Type: journal article

Data Source

IRDB

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