Photo- and PH-switchable fluorescent diarylethenes based on 2,3-diarylcyclopent-2-en-1-ones with dialkylamino groups
Source abstract
Abstract
Abstract New dialkylamino groups-comprising diarylethenes of 2,3-diarylcyclopent-2-en-1-one (DCP) series have been synthesized and its photochromic, fluorescent as well as acidochromic features have been investigated. It was shown that photochromic properties of the substances depend strong on their structures; the non-symmetry of the photochromic molecule is a powerful tool to properly control and tune the parameters of diarylethenes. It has been found that the most promising of DCPs synthesized are those containing dialkylamino groups in ethene “bridge” (rather than in aryl moieties) because they possess photo- and pH-switchable emission along with thermal stability. It has been established that the introduction at the second position of the cyclopentenone ring the benzene residue leads to the disappearance of the photochromic properties.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Photochromic and Fluorescence Chemistry · Synthesis of Indole Derivatives · Radical Photochemical Reactions
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (51)
Show source-provided references
1. Hybrid materials – past, present and future
2. Transition to organic materials science. Passive, active, and hybrid nanotechnologies10.1021/jo070543s ↗
3. Organic and hybrid molecular systems10.1016/j.mencom.2015.03.001 ↗
4. 2003
5. Feringa · 2011
6. En route to a motorized nanocar10.1021/ol060445d ↗
7. Irie · Chem Rev · 2014 · 114 · 1217410.1021/cr500249p ↗
8. Fluorescent photochromes of diarylethene series: synthesis and properties10.1070/RC2013v082n06ABEH004339 ↗
9. 2013
10. Recent progresses on diarylethene based photochromic switches10.1039/b302356g ↗
11. A highly Hg(II)-selective chemosensor with unique diarylethene fluorophore10.5012/bkcs.2010.31.5.1371 ↗
12. New photochromic chemosensors for Hg2+ and F−10.1016/j.tet.2010.12.019 ↗
13. Synthesis and photochromic and fluorescence properties of 3-(1-benzyl-5-methoxy-2-methylindolyl)-4-thienyl-substituted furan(pyrrole)-2,5-diones10.1007/s11172-014-0402-4 ↗
14. Imidazole-based dithienylethenes as a selective chemosensors for iron(III) ions10.1016/j.dyepig.2011.08.005 ↗
15. Synthesis of photochromic diarylethene polymers for a write-by-light/erase-by-heat recording system10.1016/j.tet.2008.05.088 ↗
16. Synthesis and photochromic properties of asymmetric dihetarylethenes based on 5-methoxy-1,2-dimethylindole and 5-(4-bromophenyl)-2-methylthiophene10.1007/s10593-014-1547-7 ↗
17. Visible light-triggered photoswitchable diarylethene-based iridium(iii) complexes for imaging living cells10.1002/asia.201000820 ↗
18. Reversible surface morphology changes of a photochromic diarylethene single crystal by photoirradiation10.1126/science.291.5509.1769 ↗
19. A diarylethene cocrystal that converts light into mechanical work10.1021/ja105356w ↗
20. Photoswitchable exciton coupling in merocyanine–diarylethene multi-chromophore hydrogen-bonded complexes10.1002/anie.201205504 ↗
21. Selective photoswitching of a dyad with diarylethene and spiropyran units10.1016/j.tet.2005.02.004 ↗
22. Syntheses and optoelectronic properties of four photochromic dithienylethenes10.1016/j.tet.2005.04.044 ↗
23. Rewritable volume holographic optical storage on PMMA film of diarylethene10.1117/12.581002 ↗
24. Photochemical pKa-modulation and gated photochromic properties of a novel diarylethene switch10.1002/(SICI)1099-0690(199909)1999:9<2359::AID-EJOC2359>3.0.CO;2-# ↗
25. Photomodulation of the proton affinity and acid gated photochromism of a novel dimethylaminophenyl thiazole diarylethene10.1016/j.dyepig.2011.05.006 ↗
26. Acid-induced photochromic system switching of diarylethene derivatives between P- and T-types10.1039/b700177k ↗
27. Lewis acid modulation in a amido-functional diarylethene and its hypsochromism effect10.1002/cjoc.200690275 ↗
28. Synthesis and spectral properties of a novel family of photochromic diarylethenes-2,3-diarylcyclopent-2-en-1-ones10.1016/j.jphotochem.2012.02.011 ↗
29. Synthesis and comparative photoswitching studies of unsymmetrical 2,3-diarylcyclopent-2-en-1-ones10.1021/jo500177k ↗
30. Regio- and chemoselective bromination of 2,3-diarylcyclopent-2-en-1-ones10.1021/jo301474j ↗
31. Synthesis and photochromic properties of oxime derivatives of 2,3-diarylcyclopent-2-en-1-ones10.1039/c3pp50055a ↗
32. Synthesis and spectral properties of photochromic cyclopentenone diarylethenes with an additional π-system in the ethene bridge10.1016/j.mencom.2013.09.010 ↗
33. New fluorescent switches based on photochromic 2,3-diarylcyclopent-2-en-1-ones and 6-ethoxy-3-methyl-1H-phenalen-1-one10.1016/j.dyepig.2012.12.019 ↗
34. Lonshakov · Dyes Pigments · 2014 · 109 · 10510.1016/j.dyepig.2014.04.040 ↗
35. Photochemical transformations of sulfophthaleine dyes in thin film state10.1016/1010-6030(94)80025-1 ↗
36. Trans-cis photoisomerization, fluorescence, and relaxation phenomena of trans-4-nitro-4′-(dialkylamino)stilbenes and analogues with a nonrotatable amino group10.1021/j100357a024 ↗
37. Fluorescence spectra and quantum yields. quinine, uranine, 9,10-diphenylanthracene, and 9,10-bis(phenylethynyl)anthracenes10.1021/je60062a002 ↗
38. Reference materials for fluorescence measurement10.1351/pac198860071107 ↗
39. Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism10.1021/j100248a024 ↗
40. Bis(3-thianaphthenoyl)furoxan10.1021/jo01101a023 ↗
41. Convenient synthesis of diarylpropargyl alcohols10.1016/j.mencom.2011.11.016 ↗
42. An environmentally friendly synthesis of Michler's ketone analogues in water10.1055/s-0031-1289623 ↗
43. Acylation of meldrum's acid with arylacetic acid imidazolides as a convenient method for the synthesis of 4-aryl-3-oxobutanoates10.1007/s11172-011-0019-9 ↗
44. Synthesis, biological evaluation, and receptor docking simulations of 2-[(acylamino)ethyl]-1,4-benzodiazepines as kappa-opioid receptor agonists endowed with antinociceptive and antiamnesic activity10.1021/jm0307640 ↗
45. Potential antiinflammatory compounds. 1. Antiinflammatory phenylpiperidine derivatives10.1021/jm00198a006 ↗
46. Photoinduced skeletal rearrangement of diarylethenes comprising oxazole and phenyl rings10.1021/ol502073t ↗
47. Catalytic intermolecular Pauson-Khand-type reaction: strong directing effect of pyridylsilyl and pyrimidylsilyl groups and isolation of Ru complexes relevant to catalytic reaction10.1021/ja047484+ ↗
48. Molecular design strategy toward diarylethenes that photoswitch with visible light10.1021/ja5090749 ↗
49. Substituent effect on the photochromic reactivity of bis(2-thienyl)perfluorocyclopentenes10.1016/S0040-4020(01)00389-1 ↗
50. Switching with orthogonal stimuli: electrochemical ring-closure and photochemical ring-opening of bis(thiazolyl)maleimides10.1039/C2SC21681G ↗
51. Substituent effects on the photochromic properties of benzothiophene-based derivatives10.1002/chem.201500647 ↗