Volume 42, Issue 24 pp. 3343-3348
Concise Report

Stereoselective Gridization of Ladder-Type Grids with Four Chiral Centers

Yang Li

Yang Li

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

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Yueting Pu

Yueting Pu

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

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Zheng Zhang

Zheng Zhang

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

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Fangju Tao

Fangju Tao

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

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Xiaoyan Li

Xiaoyan Li

Frontiers Science Center for Flexible Electronics (FSCFE), MIIT Key Laboratory of Flexible Electronics (KLoFE), Northwestern Polytechnical University, Xi’an, Shaanxi, 710072 China

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Jingrui Zhang

Jingrui Zhang

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

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Xin Chen

Xin Chen

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

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Yuezheng Gao

Yuezheng Gao

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

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Ying Wei

Corresponding Author

Ying Wei

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

E-mail: [email protected]; [email protected]Search for more papers by this author
Linghai Xie

Corresponding Author

Linghai Xie

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, Jiangsu, 210023 China

E-mail: [email protected]; [email protected]Search for more papers by this author
First published: 04 September 2024
Citations: 1

Comprehensive Summary

To address the stereoselective synthesis challenge in π-stacked grids with four chiral centers, we utilized coplanar and highly rigid 11,12-dihydroindeno[2,1-a]fluorene-11,12-diol and 2,2'-bithiophene as synthons, employing Friedel-Crafts gridization (FCG). Leveraging the supramolecular interactions of S···S and π···π within the thiophene moiety, along with the steric effect of the 11,12-dihydroindeno[2,1-a]fluorene scaffold, we successfully achieved the exclusive generation of a single isomer of Ladder-type π-stacked grids (LGs-IF) containing six theoretical isomers. By subsequently substituting 2,2'-bithiophene with thiophene/bithiophene derivatives as synthons, we maintained an exceptionally high level of stereoselectivity. This study introduces a novel approach for the stereo-controlled preparation of grids involving multi-chiral centers.

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