Unusual Cross-Conjugation in Cyclic Dipeptide-Based Building Blocks for Donor-Acceptor Semiconducting Conjugated Polymers.

Autor: Wang S; State Key Lab of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Functional and Intelligent Hybrid Materials and Devices, South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, 510640, Guangzhou, China., Ye F; State Key Lab of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Functional and Intelligent Hybrid Materials and Devices, South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, 510640, Guangzhou, China., Wang J; Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, School of Materials Science and Engineering, Peking University, 100871, Beijing, China., Ding R; State Key Lab of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Functional and Intelligent Hybrid Materials and Devices, South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, 510640, Guangzhou, China., Peng M; State Key Lab of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Functional and Intelligent Hybrid Materials and Devices, South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, 510640, Guangzhou, China., Li JT; Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, School of Materials Science and Engineering, Peking University, 100871, Beijing, China., Luan Y; State Key Lab of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Functional and Intelligent Hybrid Materials and Devices, South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, 510640, Guangzhou, China., Liao J; State Key Lab of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Functional and Intelligent Hybrid Materials and Devices, South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, 510640, Guangzhou, China., Guo ZH; State Key Lab of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Functional and Intelligent Hybrid Materials and Devices, South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, 510640, Guangzhou, China.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Aug 28, pp. e202413782. Date of Electronic Publication: 2024 Aug 28.
DOI: 10.1002/anie.202413782
Abstrakt: Cross conjugation, though prevalent in many organic compounds, is typically considered less effective for electron delocalization compared to linear conjugation. Consequently, it is rarely used as the backbone structure for semiconducting conjugated polymers. In this study, we designed and synthesized a novel building block, TIDP, which features a central cyclic dipeptide with cross conjugation characteristics. Strong intramolecular hydrogen bonding interactions confer TIDP with a highly rigid and coplanar conformation. Importantly, theoretical calculations reveal that π electrons are well delocalized across the entire structure, despite its low aromaticity. Conjugated polymers incorporating TIDP exhibit high charge carrier mobilities, demonstrating the effective π electrons delocalization of this innovative building block. Our findings show that with rational design, cross conjugation can achieve effective π electrons delocalization, providing a valuable approach for developing high-performance conjugated polymers for organic electronic materials.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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