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

Patrick W. Fritz, Tianyang Chen, Timur Ashirov, Anh‐Dao Nguyen, Mircea Dincă, Ali Coşkun

2022Angewandte Chemie International Edition31 citationsDOIOpen Access PDF

Abstract

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 m 2 g −1 , and exhibit light‐switchable and tunable semiconducting properties.

Topics & Concepts

CyclooctatetraeneAntiaromaticityAnthraceneSemiconductorMaterials scienceConjugated systemPlanarPorosityPorous mediumPolymerOrganic semiconductorIntermolecular forceBand gapSubject matterNanotechnologyChemical engineeringPhotochemistryMoleculeChemistryAromaticityOrganic chemistryOptoelectronicsComposite materialComputer scienceComputer graphics (images)EngineeringPedagogyCurriculumPsychologySynthesis and Properties of Aromatic CompoundsCovalent Organic Framework ApplicationsLuminescence and Fluorescent Materials
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