A Corrole-Based Covalent Organic Framework Featuring Desymmetrized Topology

Yanming Zhao; Wenhao Dai; Yunlei Peng; Zheng Niu; Qi Sun; Chuan Shan; Hui Yang; Gaurav Verma; Lukasz Wojtas; Daqiang Yuan; Zhenjie Zhang; Haifeng Dong; Xueji Zhang; Bao Zhang; Yaqing Feng; Shengqian Ma

doi:10.1002/anie.201915569

A Corrole-Based Covalent Organic Framework Featuring Desymmetrized Topology

Angew Chem Int Ed Engl. 2020 Mar 9;59(11):4354-4359. doi: 10.1002/anie.201915569. Epub 2020 Feb 3.

Authors

Yanming Zhao^{1

2

3}, Wenhao Dai⁴, Yunlei Peng⁵, Zheng Niu², Qi Sun², Chuan Shan², Hui Yang², Gaurav Verma², Lukasz Wojtas², Daqiang Yuan⁶, Zhenjie Zhang⁵, Haifeng Dong⁴, Xueji Zhang⁷, Bao Zhang¹, Yaqing Feng^{1

3}, Shengqian Ma²

Affiliations

¹ School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300350, China.
² Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, FL, 33620, USA.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, China.
⁴ Research Center for Bioengineering and Sensing Technology, University of Science & Technology Beijing, Beijing, 100083, China.
⁵ College of Chemistry, Nankai University, Tianjin, 300071, China.
⁶ State Key Laboratory of Structure Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, China.
⁷ School of Biomedical Engineering, Shenzhen University Health Science Center, Shenzhen, Guangdong, 518060, China.

PMID: 31913559
DOI: 10.1002/anie.201915569

Abstract

Herein, for the first time, we present the successful synthesis of a novel two-dimensional corrole-based covalent organic framework (COF) by reacting the unusual approximately T-shaped 5,10,15-tris(p-aminophenyl)corrole H₃ TPAPC with terephthalaldehyde, which adopts desymmetrized hcb topology and consists of a staggered AB stacking structure with elliptical pores. The resultant corrole-based COF, TPAPC-COF, exhibits high crystallinity and excellent chemical stability. The combination of extended π-conjugated backbone and interlayer noncovalent π-π interactions endows TPAPC-COF with excellent absorption capability in the entire visible-light and even near-infrared regions. Moreover, this work suggests the promise of TPAPC-COF as a new class of photoactive material for efficient singlet-oxygen generation with potential photodynamic therapy application as demonstrated by in vitro anticancer studies.

Keywords: corrole; covalent organic framework; desymmetrized topology; singlet oxygen.

Publication types

Research Support, Non-U.S. Gov't