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Reversible Isomerization of Stiff-Stilbene by an Oriented External Electric Field.

J Am Chem Soc

January 2025

Key Laboratory for Advanced Materials, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.

Understanding and effectively controlling molecular conformational changes are essential for developing responsive and dynamic molecular systems. Here, we report that an oriented external electric field (OEEF) is an effective catalyst for the cis-trans isomerization of stiff-stilbene, a key component of overcrowded alkene-based rotary motors. This reversible isomerization occurs under ambient conditions, is free from side reactions, and has been verified using ultraperformance liquid chromatography and UV-vis absorption spectroscopy.

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Vegetables containing sulfur compounds promote trans-isomerization of unsaturated fatty acids in triacylglycerols during the cooking process.

Food Res Int

January 2025

Faculty of Science & Technology, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya, Aichi 468-8502, Japan; Graduate School of Environmental and Human Sciences, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya, Aichi 468-8502, Japan. Electronic address:

Growing evidence indicates that the intake of trans-fatty acids (TFAs) has been associated with a higher risk of cardiovascular disease; therefore, various industrial measures have been taken to reduce the amount of TFAs consumed. However, research on TFAs formed during cooking is limited. Isothiocyanates and polysulfides, which are widely distributed in various vegetables, have recently been shown to promote the cis-trans isomerization of double bonds.

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Article Synopsis
  • Photoresponsive drug delivery systems offer enhanced cancer treatment but face issues with size and limited light penetration.
  • A new near infrared responsive system was created using azobenzene-modified silica nanoparticles that release a drug upon specific light excitation.
  • The design allows for targeted delivery to cancer cell nuclei, facilitating DNA damage and cell destruction, making it a promising approach for effective cancer therapy.
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The position and configuration of the C═C bond have a significant impact on the spatial conformation of unsaturated lipids, which subsequently affects their biological functions. Double bond isomerization of lipids is an important mechanism of bacterial stress response, but its in-depth mechanistic study still lacks effective analytical tools. Here, we developed a visible-light-activated dual-pathway reaction system that enables simultaneous [2 + 2] cycloaddition and catalytic - isomerization of the C═C bond of unsaturated lipids via directly excited anthraquinone radicals.

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Detailed DFT studies of H and C NMR chemical shifts of hydroxy secondary oxidation products of various geometric isomers of conjugated linolenic acids methyl esters are presented. Several low energy conformers were identified for model compounds of the central dienenol OH moiety, which were found to be practically independent on the various functionals and basis sets used. This greatly facilitated the minimization process of the geometric isomers of conjugated linolenic acids methyl esters.

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