The effect of substituent position upon unsymmetrical isomeric diarylethenes bearing a methoxy group

Dyes and Pigments

Volumn 84, Issue 1, 2010, Pages 25-35

  Pu, Shouzhi ^a   Fan, Congbin ^a   Miao, Wenjuan ^a   Liu, Gang ^a  

^a Nanchang Normal University   (China)

Author keywords

Electrochemistry; Fluorescent switch; Methoxy substituent position effect; Photochemistry; Photochromism; Unsymmetrical diarylethene

Indexed keywords

BENZENE RING; CLOSED-RING ISOMERS; CYCLIC VOLTAMMOGRAMS; CYCLOREVERSION; DIARYLETHENES; FLUORESCENT SWITCH; METHOXY GROUP; METHOXY SUBSTITUENT POSITION EFFECT; MOLAR ABSORPTION COEFFICIENT; ONE-TERMINAL; PHOTOCHEMISTRY; PHOTOCHROMIC DIARYLETHENES; PMMA FILMS; UNSYMMETRICAL; UNSYMMETRICAL DIARYLETHENE;

BEARINGS (STRUCTURAL); BENZENE; ELECTROCHEMICAL PROPERTIES; FLUORESCENCE; ISOMERS; OLEFINS; PHOTOCHROMISM; STEEL BEAMS AND GIRDERS;

ELECTROCHEMISTRY;

ABSORPTION; ELECTROCHEMISTRY; FILM; FLUORESCENCE; OXIDATION; POLYMETHYL METHACRYLATE; SYNTHESIS;

EID: 69249205358     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.06.018     Document Type: Article

References (61)

1. Dürr H., and Bouas-Laurent H. Photochromism, molecules and systems (1990), Elsevier, Amsterdam
2. Tian H., and Feng Y.L. Next step of photochromic switches?. J Mater Chem 18 (2008) 1617-1622
3. Higashiguchi K., Matsuda K., Tanifuji N., and Irie M. Full-color photochromism of a fused dithienylethene trimer. J Am Chem Soc 127 (2005) 8922-8923
4. Roxburgh C.J., and Sammes P.G. On the acid catalysed isomerisation of some substituted spirobenzopyrans. Dyes Pigments 27 (1995) 63-69
5. Traven V.F., Bochkov A.Y., Krayushkin M.M., Yarovenko V.N., Nabatov B.V., Dolotov S.M., et al. Coumarinyl(thienyl)thiazoles: novel photochromes with modulated fluorescence. Org Lett 10 (2008) 1319-1322
6. Yokoyama Y. Fulgides for memories and switches. Chem Rev 100 (2000) 1717-1740
7. Irie M. Diarylethenes for memories and switches. Chem Rev 100 (2000) 1685-1716
8. Kawata S., and Kawata Y. Three-dimensional optical data storage using photochromic materials. Chem Rev 100 (2000) 1777-1788
9. Tian H., and Yang S. Recent progresses on diarylethene based photochromic switches. J Chem Soc Rev 33 (2004) 85-97
10. Tian H., Qin B., Yao R.G., Zhao X.L., and Yang S.J. A single photochromic molecular switch with four optical outputs probing four inputs. Adv Mater 15 (2003) 2104-2107
11. Feng Y.L., Yan Y.L., Wang S., Zhu W.H., Qian S.X., and Tian H. Photochromic thiophene oligomers based on bisthienylethene: syntheses, photochromic and two-photon properties. J Mater Chem 16 (2006) 3685-3692
12. Irie M., Lifka T., Kobatake S., and Kato N. Photochromism of 1,2-bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene in a single-crystalline phase. J Am Chem Soc 122 (2000) 4871-4876
13. Yamaguchi T., Fujita Y., Nakazumi H., Kobatake S., and Irie M. Photochromic properties of diarylethene derivatives having chryso[b]thiophene rings. Tetrahedron 60 (2004) 9863-9869
14. Matsuda K., and Irie M. Diarylethene as a photoswitching unit. J Photochem Photobiol C 5 (2004) 169-182
15. Yumto K., Irie M., and Matsuda K. Control of the photoreactivity of diarylethene derivatives by quaternarization of the pyridylethynyl group. Org Lett 10 (2008) 2051-2054
16. Uchida K., Matsuoka T., Sayo K., Iwamoto M., Hayashi S., and Irie M. Thermally reversible photochromic systems. Photochromism of a dipyrrolylperfluorocyclopentene. Chem Lett (1999) 835-836
17. Yamada T., Kobatake S., Muto K., and Irie M. X-ray crystallographic study on single-crystalline photochromism of bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene. J Am Chem Soc 122 (2000) 1589-1592
18. Pu S.Z., Zhang F.S., Sun F., Wang R.J., Zhou X.H., and Chan S.K. The allomorphism of a photochromic diarylethene. Tetrahedron Lett 44 (2003) 1011-1014
19. Irie M., and Mohri M. Thermally irreversible photochromic systems. Reversible photocyclization of diarylethene derivatives. J Org Chem 53 (1988) 803-808
20. Nakamura S., and Irie M. Thermally irreversible photochromic systems. A theoretical study. J Org Chem 53 (1988) 6136-6138
21. Irie M., Sakemura K., Okinaka M., and Uchida K. Photochromism of dithienylethenes with electron-donating substituents. J Org Chem 60 (1995) 8305-8309
22. Irie M., Eriguchi T., Takada T., and Uchida K. Photochromism of diarylethenes having thiophene oligomers as the aryl groups. Tetrahedron 53 (1997) 12263-12271
23. Bens A.T., Frewert D., Kodatis K., Kryschi C., Martin H.D., and Trommsdorff H.P. Coupling of chromophores: carotenoids and photoactive diarylethenes-photoreactivity versus radiationless deactivation. Eur J Org Chem (1998) 2333-2338
24. Pu S.Z., Yang T.S., Xu J.K., Shen L., Li G.Z., Xiao Q., et al. Syntheses and optoelectronic properties of four photochromic dithienylethenes. Tetrahedron 61 (2005) 6623-6629
25. Pu S.Z., Liu G., Shen L., and Xu J.K. Efficient synthesis and properties of isomeric photochromic diarylethenes having a pyrrole unit. Org Lett 9 (2007) 2139-2142
26. Perters A., Vitols C., McDonald R., and Branda N.R. Novel photochromic compounds based on the 1-thienyl-2-vinylcyclopentene backbone. Org Lett 5 (2003) 1183-1186
27. Pu S.Z., Zheng C.H., Le Z.G., Liu G., and Fan C.B. Substituent effects on the properties of photochromic diarylethenes. Tetrahedron 64 (2008) 2576-2585
28. Yamaguchi T., Takami S., and Irie M. Photochromic properties of 1,2-bis(6-substitute-2-methyl-1-benzofuran-3-yl)ethene derivatives. J Photochem Photobiol A 193 (2008) 146-152
29. Uchida K., Matsuoka T., Kobatake S., Yamaguchi T., and Irie M. Substituent effect on the photochromic reactivity of bis(2-thienyl)perfluorocyclopentenes. Tetrahedron 57 (2001) 4559-4565
30. Perrier A., Maurel F., and Aubard J. Theoretical investigation of the substituent effect on the electronic and optical properties of photochromic dithienylethene derivatives. J Photochem Photobiol A 189 (2007) 167-176
31. Pu S.Z., Yang T.S., Xu J.K., and Chen B. Substituent position effect on the optoelectronic properties of photochromic diarylethenes. Tetrahedron Lett 47 (2006) 3167-3171
32. Fan C.B., Pu S.Z., Liu G., and Yang T.S. Substituent position effect on the properties of isomeric photochromic diarylethenes bearing chlorine atoms. J Photochem Photobiol A 194 (2008) 333-343
33. Fan C.B., Pu S.Z., Liu G., and Yang T.S. Substituent position effect on the properties of new unsymmetrical isomeric diarylethenes having a chlorine atom. J Photochem Photobiol A 197 (2008) 415-425
34. Pu S.Z., Yan L.S., Wen Z.D., Liu G., and Shen L. Synthesis and chlorine atom position effect on the properties of unsymmetrical photochromic diarylethenes. J Photochem Photobiol A 196 (2008) 84-93
35. Pu S.Z., Yang T.S., Xu J.K., and Chen B. Syntheses and properties of new photochromic diarylethene derivatives having a pyrazole unit. Tetrahedron Lett 47 (2006) 6473-6477
36. Morimitsu K., Shibata K., Kobatake S., and Irie M. Dithienylethenes with a novel photochromic performance. J Org Chem 67 (2002) 4574-4578
37. Shibata K., Kobatake S., and Irie M. Extraordinarily low cycloreversion quantum yields of photochromic diarylethenes with methoxy substituents. Chem Lett (2001) 618-619
38. Browne W.R., Jong J.J.D., Kudernac T., Walko M., Lucas L.N., Uchida K., et al. Oxidative electrochemical switching in dithienylcyclopentenes, part 2: effect of substitution and asymmetry on the efficiency and direction of molecular switching and redox stability. Chem Eur J 11 (2005) 6430-6441
39. Myles A.J., Wigglesworth T.J., and Branda N.R. A multi-Addressable photochromic 1,2-dithienylcyclopentene-phenoxynaphthacenequinone hybrid. Adv Mater 15 (2003) 745-748
40. Yang T.S., Pu S.Z., Chen B., and Xu J.K. Electron-donating methoxy group position effect on properties of diarylethene derivatives having a pyrazole unit. Can J Chem 85 (2007) 12-20
41. Pu S.Z., Liu G., Li G.Z., Wang R.J., and Yang T.S. Synthesis, crystal structure and its optical and electrochemical properties of a new unsymmetrical diarylethene. J Mol Struct 833 (2007) 23-29
42. Pu S.Z., Liu G., Chen B., and Wang R.J. 1-(2-Methyl-5-phenyl-3-thienyl)-2-(3-methyl-5-phenyl-2-thien)-3,3,4,4,5,5-hexa-1-ene: a novel photochromic hybrid diaryl. Acta Cryst C 61 (2005) o599-o601
43. Gilat S.L., Kawai S.H., and Lehn J.-M. Light-triggered molecular devices: photochemical switching of optical and electrochemical properties in molecular wire type diarylethene species. Chem Eur J 1 (1995) 275-284
44. Li Z.X., Liao L.Y., Sun W., Xu C.H., Zhang C., Fang C.J., et al. Reconfigurable cascade circuit in a photo- and chemical-switchable fluorescent diarylethene derivative. J Phys Chem C 112 (2008) 5190-5196
45. Yang T.S., Pu S.Z., Fan C.B., and Liu G. Synthesis, crystal structure and optoelectronic properties of a new unsymmetrical photochromic diarylethene. Spectrochim Acta A 70 (2008) 1065-1072
46. Kasatani K., Kambe S., and Irie M. Photochromic reaction and fluorescence of dithienylethenes in the solid state. J Photochem Photobiol A 122 (1999) 11-15
47. Hansch C., Leo A., and Taft R.W. A survey of Hammett substituent constants and resonance and field parameters. Chem Rev 91 (1991) 165-195
48. Morimoto M., Kobatake S., and Irie M. Polymorphism of 1,2-bis(2-methyl-5-p-methoxyphenyl-3-thienyl)perfluorocyclopentene and photochromic reactivity of the single crystals. Chem Eur J 9 (2003) 621-627
49. Kobatake S., Uchida K., Tsuchida E., and Irie M. Single-crystalline photochromism of diarylethenes: reactivity-structure relationship. Chem Commun (2002) 2804-2805
50. Morimoto M., and Irie M. Photochromism of diarylethene single crystals: crystal structures and photochromic performance. Chem Commun (2005) 3895-3905
51. Woodward R.B., and Hoffmann R. The conservation of orbital symmetry (1970), Verlag Chemie, Weinheim, Germany GmbH
52. Morimoto M., and Irie M. Photochromic reactions of diarylethenes in single crystals with intermolecular O-H[rId9][rId9][rId9]N hydrogen-bonding networks. Chem Eur J 12 (2006) 4275-4282
53. Ramamurthy V., and Venkatesan K. Photochemical reactions of organic crystals. Chem Rev 87 (1987) 433-481
54. Irie M., Fukaminato T., Sasaki T., Tamai N., and Kawai T. A digital fluorescent molecular photoswitch. Nature 420 (2002) 759-760
55. Sworakowski J., Janus K., and Nešpůrek S. Kinetics of photochromic reactions in condensed phases. Adv Colloid Interface Sci 116 (2005) 97-110
56. Giordano L., Jovin T.M., Irie M., and Jares-Erijman E.A. Diheteroarylethenes as thermally stable photoswitchable acceptors in photochromic fluorescence resonance energy transfer (pcFRET). J Am Chem Soc 124 (2002) 7481-7489
57. Norsten T.B., and Branda N.R. Photoregulation of fluorescence in a porphyrinic dithienylethene photochrome. J Am Chem Soc 123 (2001) 1784-1785
58. Fölling J., Polyakova S., Belov V., Blaaderen A., Bossi M.L., and Hell S.W. Synthesis and characterization of photoswitchable fluorescent silica nanoparticles. Small 4 (2008) 134-142
59. Gorodetsky B., Samachetty H.D., Donkers R.L., Workentin M.S., and Branda N.R. Reductive electrochemical cyclization of a photochromic 1,2-dithienylcyclopentene dication. Angew Chem Int Ed 43 (2004) 2812-2815
60. Peters A., and Branda N.R. Electrochromism in photochromic dithienylcyclopentenes. J Am Chem Soc 125 (2003) 3404-3405
61. Moriyama Y., Matsuda K., Tanifuji N., Irie S., and Irie M. Electrochemical cyclization/cycloreversion reactions of diarylethenes. Org Lett 7 (2005) 3315-3318