Characteristics and long-term kinetics of an azobenzene derivative and a donor–acceptor Stenhouse adduct as orthogonal photoswitches

Schmitt, Tanja; Huck, Christian; Oberhof, Nils; Hsu, Li-Yun; Blasco, Eva; Dreuw, Andreas; Tegeder, Petra

doi:10.1039/d3cp05786k

Phys. Chem. Chem. Phys.

2024

DOI: 10.1039/d3cp05786k

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Characteristics and long-term kinetics of an azobenzene derivative and a donor–acceptor Stenhouse adduct as orthogonal photoswitches

Tanja Schmitt,

Christian Huck,

Nils Oberhof

et al.

Abstract: Light-triggered molecular switches are extensively researched for their applications in medicine, chemistry and material science and, if combined, particularly for their use in multifunctional smart materials, for which orthogonally, i.e....

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Cited by 2 publications

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Advancing Optoglycomics: Two Orthogonal Azobenzene Glycoside Antennas in One Glycocluster–Synthesis, Switching Cycles, Kinetics and Molecular Dynamics

Friedrich,

Hartke,

Lindhorst

2024

Chemistry A European J

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Carbohydrate recognition is essential for numerous biological processes and is governed by various factors within the supramolecular environment of the cell. Photoswitchable glycoconjugates have proven as valuable tools for the investigation and modulation of carbohydrate recognition as they allow to control the relative orientation of sugar ligands by light. We have synthesized a biantennary glycocluster in which two glycoazobenzene antennas are conjugated to the 3‐ and 6‐position of a scaffold glycoside. Orthogonal isomerization of the photoswitchable units was made possible by the different conjugation of the azobenzene moieties via an oxygen and a sulfur atom, respectively, and the ortho‐fluorination of one of the azobenzene units. This design enabled a switching cycle comprising the EE, EZ and the ZZ isomer. This is the first example of an orthogonally photoswitchable glycocluster. The full analysis of its photochromic properties included the investigation of the isolated glycoazobenzene antennas allowing the comparison of the intra‐ versus the intermolecular orthogonal photoswitching. The kinetics of the thermal relaxation were analyzed in detail. A molecular dynamics study shows that indeed, the relative orientation of the glycoantennas and the distances between the terminal sugar ligands significantly vary depending on the isomeric state, as intended.

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Advancing Optoglycomics: Two Orthogonal Azobenzene Glycoside Antennas in One Glycocluster–Synthesis, Switching Cycles, Kinetics and Molecular Dynamics

Friedrich,

Hartke,

Lindhorst

2024

Chemistry A European J

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Synthesis, DFT, In Silico ADME, and Antimicrobial Study of New 2‐(aryl)‐5‐(3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐Oxadiazoles

Dhonnar,

Buchude,

Sargade

et al. 2024

ChemistrySelect

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The rise of drug‐resistant infections highlights the critical need to discover novel drugs to combat them. In this study, we present the synthesis of a novel 2‐(aryl)‐5‐(3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐oxadiazole compounds (3a–b) using benzohydrazide (1a–b) and 3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazole‐4‐carboxylic acid (2). The structures of compounds were confirmed by FT‐IR, 1H‐NMR, 13C‐NMR, and HRMS characterizations. DFT calculations were performed using B3LYP/6–311G(d,p) method. The HOMO‐LUMO energy gap, reactivity parameters, and Mulliken atomic charges were determined and discussed. The electrostatic potential surface was mapped to identify active sites in compounds. The electronic absorption spectra were obtained in a chloroform solvent, and the Uv‐vis band assignments were discussed through TD‐DFT simulations. The results obtained from the experiment correspond well with the theoretical DFT analysis. The assessment of synthesized compounds (3a–b) antimicrobial properties is another aspect of the current investigation. Compound 3a was equally efficient as chloramphenicol against E. coli, P. aeruginosa, and S. pyogenes. However, limited antifungal activity was observed for both compounds. The Molinspiration ADME online tool examines drugs likeness properties.

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Characteristics and long-term kinetics of an azobenzene derivative and a donor–acceptor Stenhouse adduct as orthogonal photoswitches

Abstract: Light-triggered molecular switches are extensively researched for their applications in medicine, chemistry and material science and, if combined, particularly for their use in multifunctional smart materials, for which orthogonally, i.e....

Cited by 2 publications

References 46 publications

Advancing Optoglycomics: Two Orthogonal Azobenzene Glycoside Antennas in One Glycocluster–Synthesis, Switching Cycles, Kinetics and Molecular Dynamics

Advancing Optoglycomics: Two Orthogonal Azobenzene Glycoside Antennas in One Glycocluster–Synthesis, Switching Cycles, Kinetics and Molecular Dynamics

Synthesis, DFT, In Silico ADME, and Antimicrobial Study of New 2‐(aryl)‐5‐(3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐Oxadiazoles

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