Remote-controlled regio- and diastereodifferentiating photodimerization of a dynamic helical peptide-bound 2-substituted anthracene

Taura, Daisuke; Urushima, Akio; Sugioka, Yusuke; Ousaka, Naoki; Yashima, Eiji

doi:10.1039/d0cc06164f

Cited by 3 publications

(1 citation statement)

References 45 publications

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“…In recent years, smart materials have been studied extensively for their important applications in molecular switches, − white light-emitting diodes, − information storage, , anti-counterfeiting, , separation and detection, − drug delivery, , and other fields. − Smart material molecules can reversibly change their physical and chemical properties under different external stimuli. , Among various external stimuli, including light energy, electrical energy, and chemical energy, light is the most suitable and convenient source of clean energy and has advantages of precise control as a stimulus source and energy-saving and environmental protection characteristics. Previously reported light stimulation of smart molecules includes the trans-to-cis isomerization of azobenzene and stilbene derivatives, − photocyclization of diarylethylenes, − [2 + 2] cycloaddition of alkenes, − and [4 + 4] photodimerization of anthracene. − Photoinduced trans-to-cis isomerization has attracted much attention in inorganic and organic chemistry, materials science, and biology. Photoinduced trans-to-cis isomerization is the reversible conversion of trans isomers to cis isomers under a certain light wavelength. , Isomers with different molecular structures have different physical and chemical properties (including magnetic, optical, and electrical properties), which can be controlled by illumination.…”

Section: Introductionmentioning

confidence: 99%

Insights into the Effect of Trans-to-Cis Photoisomerization of a Co-coordinated Stilbene Derivative on the Luminescence of Di-β-diketonate Lanthanide Complexes

Tan

Hou

et al. 2021

ACS Omega

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Five lanthanide complexes constructed from a stilbene derivative, (E)-N′,N′-bis(pyridin-2-ylmethyl)-4-styrylbenzoyl hydrazide (HL), and two β-diketonates (2-thenoyltrifluoroacetonate, tta), with or without a trifluoroacetate anion (CF3CO2 –), namely, [Ln(tta)2(HL) (CF3CO2)] [LnC45H32F9N4O7S2, Ln = La (1), Nd (2), Eu (3), or Gd (4)] and [Yb(tta)2(L)] (YbC43H31F6N4O5S2 (5), L = deprotonated HL), were synthesized and characterized. Crystals of these five complexes were obtained and analyzed by single-crystal X-ray diffraction. These complexes all belonged to the monoclinic P21/c space group. For La3+, Nd3+, Eu3+, and Gd3+, the central lanthanide ion was nine-coordinate with a monocapped twisted square antiprism polyhedron geometry. The central Yb3+ ion of complex 5 was eight-coordinate with a distorted double-capped triangular prism polyhedron geometry. Among the five complexes, trans-to-cis photoisomerization of the stilbene group in gadolinium complex 4 showed the largest quantum yield. Complexes 2, 3, and 4 showed dual luminescence and photoisomerization functions. The luminescence change of complex 3 was reversible upon the trans-to-cis photoisomerization process. The sensitization efficiencies of luminescent europium complex 3 in acetonitrile solutions and in the solid state were 49.9 and 42.6%, respectively. These medium sensitization efficiencies led to the observation of simultaneous photoisomerization and luminescence, which further confirmed our previous report that photoisomerization of the stilbene group within complexes was related to the lanthanide ion energy level and whether a ligand-to-metal center or ligand-to-ligand charge-transfer process was present. In complexes 1–5, in addition to the intramolecular absorption transition of the ligand itself (IL, πHL–πHL * and πtta–πtta*), the presence of a ligand-to-ligand charge-transfer transition between tta and HL (LLCT, πtta–πHL * or πHL–πtta *) indicated whether the triplet-state energy of HL was able to transfer to the excited energy level of the lanthanide ions, leading to different extents of HL photoisomerization. These results provide an important route for the design of new dual-function lanthanide-based optical switching materials.

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Section: Introductionmentioning

confidence: 99%

Insights into the Effect of Trans-to-Cis Photoisomerization of a Co-coordinated Stilbene Derivative on the Luminescence of Di-β-diketonate Lanthanide Complexes

Tan

Hou

et al. 2021

ACS Omega

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Supramolecular Architecture of an Amphiphilic Amino Alcohol as a Versatile Chiral Environment for Stereocontrolled Photoreaction of Various Anthracenes

Kanai

Yamada

Salikolimi

et al. 2022

Chemistry A European J

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The photocyclodimerization of 2-anthracenecarboxylic acid has been extensively studied as a model reaction of asymmetric photochemistry. So far, numerous chiral environments have been employed to control this photoreaction, while the scope of photoreactants has been limited only to 2anthracenecarboxylic acid and its simple esters and amides.Here, we developed a systematic series of photoreactants (2 a-d) by introducing various substituents to 2-anthracenecarboxylic acid, which showed different reactivities and selectivities depending on the substituents. By using the photoreactants 2 a-d, we evaluated the performance of a chiral environment composed of an amphiphilic amino alcohol (1), where the photocyclodimerization of 2 a-d generally proceeded in excellent regio-and enantioselectivities (71-98 % regio ratio, 76-86 % ee). Furthermore, by reacting 2 a and 2 b together in the chiral environment of 1, we succeeded in the first stereocontrolled cross-photocyclodimerization between two prochiral anthracenes (58 % chemo ratio, 83 % regio ratio, 90 % ee).

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Photoresponsive peptide materials: Spatiotemporal control of self-assembly and biological functions

Matsuura,

Inaba

2023

Biophysics Reviews

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Peptides work as both functional molecules to modulate various biological phenomena and self-assembling artificial materials. The introduction of photoresponsive units to peptides allows the spatiotemporal remote control of their structure and function upon light irradiation. This article overviews the photoresponsive peptide design, interaction with biomolecules, and applications in self-assembling materials over the last 30 years. Peptides modified with photochromic (photoisomerizable) molecules, such as azobenzene and spiropyran, reversibly photo-controlled the binding to biomolecules and nanostructure formation through self-assembly. Photocleavable molecular units irreversibly control the functions of peptides through cleavage of the main chain and deprotection by light. Photocrosslinking between peptides or between peptides and other biomolecules enhances the structural stability of peptide assemblies and complexes. These photoresponsive peptides spatiotemporally controlled the formation and dissociation of peptide assemblies, gene expressions, protein–drug interactions, protein–protein interactions, liposome deformation and motility, cytoskeleton structure and stability, and cell functions by appropriate light irradiation. These molecular systems can be applied to photo-control biological functions, molecular robots, artificial cells, and next-generation smart drug delivery materials.

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Remote-controlled regio- and diastereodifferentiating photodimerization of a dynamic helical peptide-bound 2-substituted anthracene

Abstract: Photodimerization of a right-handed 310-helical nonapeptide-bound 2-substituted anthracene produced the chiral head-to-head anti-photodimer with up to 97% diastereomeric excess.

Cited by 3 publications

References 45 publications

Insights into the Effect of Trans-to-Cis Photoisomerization of a Co-coordinated Stilbene Derivative on the Luminescence of Di-β-diketonate Lanthanide Complexes

Insights into the Effect of Trans-to-Cis Photoisomerization of a Co-coordinated Stilbene Derivative on the Luminescence of Di-β-diketonate Lanthanide Complexes

Supramolecular Architecture of an Amphiphilic Amino Alcohol as a Versatile Chiral Environment for Stereocontrolled Photoreaction of Various Anthracenes

Photoresponsive peptide materials: Spatiotemporal control of self-assembly and biological functions

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