Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks

Huang, Hui; Yang, Lei; Facchetti, Antonio; Marks, Tobin J.

doi:10.1021/acs.chemrev.7b00084

Cited by 804Organic Electronics and PhotovoltaicsCrystallography and molecular interactionsSynthesis and Properties of Aromatic Compounds

Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks

Huang, Hui, Yang, Lei, Facchetti, Antonio, Marks, Tobin J.·2017·Chemical Reviews

DOI 10.1021/acs.chemrev.7b00084

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Abstract

Constructing highly planar, extended π-electron systems is an important strategy for achieving high-mobility organic semiconductors. In general, there are two synthetic strategies for achieving π-conjugated systems with high planarity. The conventional strategy connects neighboring aromatic rings through covalent bonds to restrict the rotation about single bonds. However, this usually requires a complex sequence of synthetic steps to achieve this target, which can be costly and labor-intensive. More recently, noncovalent through-space intramolecular interactions, which are defined here as noncovalent conformational locks, have been employed with great success to increase the planarity and rigidity of extended π-electron systems; this has become a well-known and important strategy to design and synthesize highly planar π-conjugated systems for organic electronics. This review offers a comprehensive and general summary of conjugated systems with such noncovalent conformational locks, including O···S, N···S, X···S (where X = Cl, Br, F), and H···S through-space interactions, together with analysis by density functional theory computation, X-ray diffraction, and microstructural characterization, as well as by evaluation of charge transport in organic thin-film transistors and solar cells.

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The planar architecture of 4F is attributed to an intramolecular noncovalent S···O conformational lock.
“The interaction region indicator attributes the planar architecture of 4F to an intramolecular noncovalent S···O conformational lock (Fig. 2c)34–36.”
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Alkoxy-Functionalized Bithiophene/thiazoles: Versatile Building Blocks for High-Performance Organic and Polymeric Semiconductors
Yang, K., Chen, Z., Wang, Y., & Guo, X. (2023) · Accounts of Materials Research · doi:10.1021/accountsmr.2c00237 · Cited by 72 · see citing works
Alleviating NIR-II emission quenching in ring-fused fluorophore via manipulating dimer populations for superior fluorescence imaging
Miao, X., Jia, M., Weng, X., Zhang, J., Pan, Y., Zhao, H., Yu, Z., Fan, Q., & Hu, W. (2025) · Light: Science & Applications · doi:10.1038/s41377-025-01787-0 · Cited by 25 · see citing works

Authors: Huang, H., Yang, L., Facchetti, A., & Marks, T. J.
Affiliations: Chinese Academy of Sciences (CN)
Northwestern University (US)
Corresponding author: Huang, Hui
Facchetti, Antonio
Marks, Tobin J.
ORCID: Huang, Hui
Yang, Lei
Facchetti, Antonio
Marks, Tobin J.
Venue: Chemical Reviews
Publisher: American Chemical Society (ACS)
Published: 2017-07-03
Volume: 117
Issue: 15
Pages: 10291-10318
ISSN: 0009-2665 (ISSN-L)
1520-6890
DOI: 10.1021/acs.chemrev.7b00084
OpenAlex: W2731260437
Cited by: 804
References: 162
Citations by year: 2026: 55 · 2025: 91 · 2024: 101 · 2023: 99 · 2022: 113 · 2021: 101 · 2020: 84 · 2019: 79 · 2018: 69 · 2017: 12
FWCI: 3.04
Type: journal article
Language: en
Open access: closed
Locations: Chemical Reviews (publishedVersion)
PubMed (publishedVersion)
Funders: Natural Science Foundation of Beijing Municipality (2162043)
Air Force Office of Scientific Research (FA9550-15-1-0044)
National Natural Science Foundation of China (21574135, 51303180)
Division of Materials Research (DMR-1121262)
Chinese Academy of Sciences
Topics: Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Electronics and Photovoltaics
Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Crystallography and molecular interactions
Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
Keywords: through-space interactions, organic semiconductors, semiconducting polymers, π-conjugated systems, planarity, intramolecular interactions, charge transport, organic thin-film transistors, organic solar cells, molecular rigidity

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Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks

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