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

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

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

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.

Original language	English (US)
Article number	e202116527
Journal	Angewandte Chemie - International Edition
Volume	61
Issue number	17
DOIs	https://doi.org/10.1002/anie.202116527
State	Published - Apr 19 2022
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

Keywords

Doping
Porous Organic Polymers
Post-Synthetic Modification
Semiconductors
Tetraoxa[8]Circulenes

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10.1002/anie.202116527

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title = "Fully Conjugated Tetraoxa[8]circulene-Based Porous Semiconducting Polymers",

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",

author = "Fritz, {Patrick W.} and Tianyang Chen and Timur Ashirov and Nguyen, {Anh Dao} and Mircea Dinc{\u a} and Ali Coskun",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

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doi = "10.1002/anie.202116527",

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AU - Fritz, Patrick W.

AU - Chen, Tianyang

AU - Ashirov, Timur

AU - Nguyen, Anh Dao

AU - Dincă, Mircea

AU - Coskun, Ali

PY - 2022/4/19

Y1 - 2022/4/19

N2 - 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.

AB - 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.

KW - Doping

KW - Porous Organic Polymers

KW - Post-Synthetic Modification

KW - Semiconductors

KW - Tetraoxa[8]Circulenes

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ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

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