Solid-state photochromic properties, mechanism and electrospun membranes of (E)-2-(benzo[b]thiophen-2-ylmethylene)-N-ethylhydrazine-1-carbothioamide
Source abstract
Abstract
Abstract Three carbothioamide derivatives with reversible P-type photochromic properties in the solid state were synthesized in a one-step reaction. Based on the single crystal structures, the FT-IR spectra and theory calculations, the proposed photochromic mechanism was the intermolecular proton transfer between the thio-keto and thio-enol tautomer. Nanofibrous membranes were prepared by electrospinning, which showed improved reversible photochromic properties in comparison of the compound itself. This work may open a new pathway for design and synthesis of the new solid-state photochromic materials with high-performance.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Photochromic and Fluorescence Chemistry · Porphyrin and Phthalocyanine Chemistry · Polyoxometalates: Synthesis and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (37)
Show source-provided references
1. Acylhydrazones as widely tunable photoswitches10.1021/jacs.5b09519 ↗
2. Photochromic materials: more than meets the eye10.1002/adma.201201521 ↗
3. Second-order nonlinear optical switching with a record-high contrast for a photochromic and thermochromic bistable crystal10.1039/C7SC01228D ↗
4. Simple hydrazone building blocks for complicated functional materials10.1021/ar500111f ↗
5. Photo- and proton-dual-responsive fluorescence switch based on a bisthienylethene-bridged naphthalimide dimer and its application in security data storage10.1002/ejoc.200601122 ↗
6. Coupling carbon nanomaterials with photochromic molecules for the generation of optically responsive materials10.1038/ncomms11118 ↗
7. Photochromic electret: a new tool for light energy harvesting10.1021/jz2014506 ↗
8. Substituent effect in the photochromism of two isomeric asymmetric diarylethenes having pyrrole and thiophene units10.1016/j.saa.2016.09.029 ↗
9. Improving the fatigue resistance of diarylethene switches10.1021/ja513027s ↗
10. “Photochemical oscillator”: colored hydrodynamic oscillations and waves in a photochromic system10.1021/jp407393h ↗
11. ElectrocatalyticZ→EIsomerization of azobenzenes10.1021/jacs.6b10822 ↗
12. Synthesis and optical properties of aqueous soluble indolylfulgimides10.1021/jo900909d ↗
13. Photochromic fused-naphthopyrans without residual color10.1021/jo3003216 ↗
14. Disclosing whole reaction pathways of photochromic 3H-naphthopyrans with fast color fading10.1021/acs.jpclett.6b03068 ↗
15. Excited state intramolecular proton transfer (ESIPT) in the photoresponsive prototropic schiff-base N′-(2-hydroxybenzylidene)-4-hydroxybenzohydrazide: computational modeling study10.1016/j.molstruc.2017.05.048 ↗
16. Multiresponsive photo-, solvato-, acido-, and ionochromic Schiff base probe10.1021/acs.jpcc.5b02884 ↗
17. A novel solid-state photochromic compound containing double heterocycles10.1016/j.jphotochem.2013.06.021 ↗
18. Synthesis, photoisomerization properties and thermal bleaching kinetics of pyrazolones containing 3-cyanobenzal10.1016/j.saa.2015.04.001 ↗
19. Photochromic naphthopyrans10.1016/B978-044452176-7/50004-8 ↗
20. The first structural and spectroscopic characterisation of a ring-opened form of a 2H-naphtho[1,2-b]pyran: a novel photomerocyanine10.1039/c4cc03435j ↗
21. Photochromism and thermochromism of Schiff bases in the solid state: structural aspects
22. Photochromic reaction and fluorescence of dithienylethenes in the solid state10.1016/S1010-6030(99)00016-7 ↗
23. New spiropyrans showing crystalline-state photochromism10.1002/(SICI)1521-4095(200001)12:1<48::AID-ADMA48>3.0.CO;2-G ↗
24. Photochromic organic–inorganic hybrid materials10.1039/c0cs00065e ↗
25. Aiken · 2008
26. Preparing photochromic nanofibers and animal cells using a photochromic compound of 1′,3′,3′-trimethyl-6-nitrospiro (2H-1-benzopyran-2,2′-indoline)10.1016/j.colsurfb.2011.08.024 ↗
27. Molecular docking and QSAR analyses of aromatic heterocycle thiosemicarbazone analogues for finding novel tyrosinase inhibitors10.1016/j.bioorg.2017.07.002 ↗
28. A series of α-heterocyclic carboxaldehyde thiosemicarbazones inhibit topoisomerase IIα catalytic activity10.1021/jm9014394 ↗
29. A novel series of thiosemicarbazone drugs: from synthesis to structure10.1016/j.saa.2014.08.146 ↗
30. Photoisomerization and thermoisomerization I: unusual photochromism of N-(3,5-di-tert-butyl-salicylidene) amines10.1016/0047-2670(85)87020-9 ↗
31. Coordination behavior and Biopotency of N and S/O donor ligands with their palladium(II) and platinum(II) complexes10.1007/BF03245778 ↗
32. Synthesis, characterization, and X-ray crystal structures of copper(II) and nickel(II) complexes with two bis(thiosemicarbazone) ligands and investigation of their electrochemical behavior10.1007/s11243-015-9997-z ↗
33. Structural, thermogravimetric, B3LYP and biological studies on some heterocyclic thiosemicarbazide copper (II) complexes and evaluation of their molecular docking10.1016/j.molstruc.2017.09.035 ↗
34. Photochemical isomerizations of thiosemicarbazide, a matrix isolation study10.1021/jp305995k ↗
35. Multistep photoinduced proton transfer in crystalline 2-2',4'-dinitrobenzyl/pyridine10.1016/S0301-0104(99)00317-1 ↗
36. Size-controlled conformal nanofabrication of biotemplated three-dimensional TiO2 and ZnO nanonetworks10.1038/srep02306 ↗
37. Platinum nanowires produced by electrospinning10.1021/nl802910h ↗