Pd(ii)-catalyzed enantioselective C-H olefination and photoregulation of sterically hindered diarylethenes.

Autor:	Zhang G; Key Laboratory for Advanced Material, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology Shanghai 200237 China whzhu@ecust.edu.cn mengqi15@126.com., Wu X; Department Center of Chemistry for Frontier Technologies, Department of Chemistry Zhejiang University Hangzhou 310027 China bfshi@zju.edu.cn., Mao S; Department Center of Chemistry for Frontier Technologies, Department of Chemistry Zhejiang University Hangzhou 310027 China bfshi@zju.edu.cn., Li M; Key Laboratory for Advanced Material, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology Shanghai 200237 China whzhu@ecust.edu.cn mengqi15@126.com., Hu H; Key Laboratory for Advanced Material, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology Shanghai 200237 China whzhu@ecust.edu.cn mengqi15@126.com., Shi BF; Department Center of Chemistry for Frontier Technologies, Department of Chemistry Zhejiang University Hangzhou 310027 China bfshi@zju.edu.cn., Zhu WH; Key Laboratory for Advanced Material, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology Shanghai 200237 China whzhu@ecust.edu.cn mengqi15@126.com.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2024 Nov 07. Date of Electronic Publication: 2024 Nov 07.
DOI:	10.1039/d4sc05375c
Abstrakt:	Sterically hindered diarylethenes with intrinsic chirality have shown great potential in chiral signal regulation, light-controlled liquid crystals (LCs), etc. Their unique enantiospecific phototransformation between axial chirality of ring-open isomers and central chirality of ring-closed isomers can break through the bottleneck of interference between multiple chiral centers in traditional chiral diarylethenes. However, these intrinsic chiral diarylethenes require necessary chiral resolution through preparative chiral HPLC, typically resulting in limited separation efficiency and production scale. Here, we present an enantioselective olefination strategy to directly construct intrinsic chiral diarylethenes from a prochiral sterically hindered diarylethene, achieving high yields and enantioselectivity. The resulting isomers can be further decorated by incorporating mesogenic units, and the derivatives enable the successful reversible photoregulation of blue, green, and red reflection colors of LCs with excellent thermal stability, fatigue resistance, and little texture disorderliness, demonstrating the practical application potential of direct enantioselective olefination in photoregulation with intrinsic chiral diarylethenes. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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