Fully Conjugated Tetraoxa[8]circulene-Based Porous Semiconducting Polymers

Patrick W Fritz; Tianyang Chen; Timur Ashirov; Anh-Dao Nguyen; Mircea Dincă; Ali Coskun

doi:10.1002/anie.202116527

Fully Conjugated Tetraoxa[8]circulene-Based Porous Semiconducting Polymers

Angew Chem Int Ed Engl. 2022 Apr 19;61(17):e202116527. doi: 10.1002/anie.202116527. Epub 2022 Feb 28.

Authors

Patrick W Fritz¹, Tianyang Chen², Timur Ashirov¹, Anh-Dao Nguyen¹, Mircea Dincă², Ali Coskun¹

Affiliations

¹ Department of Chemistry, University of Fribourg, Chemin du Musée 9, 1700, Fribourg, Switzerland.
² Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave, Cambridge, MA 02139, USA.

Abstract

Tetraoxa[8]circulenes (TOCs) are a class of hetero[8]circulenes featuring a planar cyclooctatetraene core with a mixed aromatic/antiaromatic motif that governs their electronic properties. Polymeric TOCs (pTOCs) have been the subject of several computational simulations because they are predicted to be low-band-gap semiconductors, but they have not been available synthetically yet. Here, we report the first example of pTOCs, a new family of porous semiconductors, synthesized under ionothermal conditions through the intermolecular cyclization of 1,4,5,8-anthracene tetrone. pTOCs are porous, with surface areas up to 1656 m² g^-1 , and exhibit light-switchable and tunable semiconducting properties.

Keywords: Doping; Porous Organic Polymers; Post-Synthetic Modification; Semiconductors; Tetraoxa[8]Circulenes.

Abstract

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