Carbon dioxide and water as a key for unlocking photochromism of diarylethene derivative

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 215, Issue 1, 2010, Pages 103-107

  Liu, Huan Huan ^a   Chen, Yi ^a  

^a TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

Diarylethene; Gate reactivity; Multi color; Multi responsive system; Photochromism

Indexed keywords

EID: 77956610472     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2010.08.002     Document Type: Article

References (45)

1. J.C. Crano, and R.J. Guglielmetti Organic Photochromic and Thermochromic Compounds 1999 Plenum Press New York
2. M. Irie Diarylethenes for memories and switches Chem. Rev. 100 2000 1685 1716
3. H. Tian, and S. Yang Recent progresses on diarylethene based photochromic switches Chem. Soc. Rev. 33 2004 85 97
4. B.L. Feringa Molecular Switches 2001 Wiley-VCH Weinheim
5. S. Kawata, and Y. Kawata Three-dimensional optical data storage using photochromic materials Chem. Rev. 100 2000 1777 1788
6. K.S. Schanze Optical Sensors and Switches 2001 Marcel Dekker New York
7. Z. Sekkat, and W. Knoll Photoreactive Organic Thin Films 2002 Academic Press London
8. A.J. Myles, T.J. Wigglesworth, and N.R. Branda A multi-addressable photochromic 1,2-dithienylcyclopentene-phenoxynaphthacenequinone hybrid Adv. Mater. 15 2003 745 748
9. K. Higashiguchi, K. Matsuda, and M. Irie Photochromic reaction of a fused dithienylethene: multicolor photochromism Angew. Chem. Int. Ed. 42 2003 3537 3540
10. H. Tian, and Y. Feng Next step of photochromic switches J. Mater. Chem. 18 2008 1617 1622
11. T. Fukaminato, T. Doi, M. Tanaka, and M. Irie Photocyclization reaction of diarylethene-perylenebisimide dyads upon irradiation with visible (>500 nm) light J. Phys. Chem. C 113 2009 11623 11627
12. I.A. Mikhailov, K.D. Belfield, and A.E. Masunov DFT-based methods in the design of two-photon operated molecular switches J. Phys. Chem. A 113 2009 7080 7089
13. C.-J. Carling, J.-C. Boyer, and N.R. Branda Remote-control photoswitching using NIR light J. Am. Chem. Soc. 131 2009 10838 10839
14. W. Tan, Q. Zhang, J. Zhang, and H. Tian Near-infrared photochromic diarylethene iridium (III) complex Org. Lett. 11 2009 161 164
15. K. Morinaka, T. Ubukata, and Y. Yokoyama Structurally versatile novel photochromic bisarylindenone and its acetal: achievement of large cyclization quantum yield Org. Lett. 11 2009 3890 3893
16. V.W.-W. Yam, J.K.-W. Lee, C.-C. Ko, and N. Zhu Photochromic diarylethene-containing ionic liquids and N-heterocyclic carbenes J. Am. Chem. Soc. 131 2009 912 913
17. Z. Zhou, S. Xiao, J. Xu, Z. Liu, M. Shi, T. Yi, and C. Huang Modulation of the photochromic property in an organoboron-based diarylethene by a fluoride ion Org. Lett. 8 2006 3911 3914
18. Y. Moriyama, K. Matsuda, N. Tanifuji, S. Irie, and M. Irie Electrochemical cyclization/cycloreversion reactions of diarylethenes Org. Lett. 7 2005 3315 3318
19. A. Peters, and N.R. Branda Electrochromism in photochromic dithienylcyclopentenes J. Am. Chem. Soc. 125 2003 3404 3405
20. N. Tanifuji, M. Irie, and K. Matsuda New photoswitching unit for magnetic interaction: diarylethene with 2,5-bis(arylethynyl)-3-thienyl group J. Am. Chem. Soc 127 2005 13344 13353 (Pubitemid 41377631)
21. K. Matsuda, and M. Irie A diarylethene with two nitronyl nitroxides: photoswitching of intramolecular magnetic interaction J. Am. Chem. Soc. 122 2000 7195 7201
22. M. Morimoto, S. Kobatake, and M. Irie Multicolor photochromism of two- and three-component diarylethene crystals J. Am. Chem. Soc. 125 2003 11080 11087
23. H. Tian, R. Qin, X. Zhao, and S. Yang A single photochromic molecular switch with four optical outputs probing four inputs Adv. Mater. 15 2003 2104 2107
24. T.J. Wigglesworth, and N.R. Branda A family of multiaddressable, multicolored photoresponsive copolymers prepared by ring-opening metathesis polymerization Chem. Mater. 17 2005 5473 5480
25. T. Nakashima, K. Miyamura, T. Sakai, and T. Kawai Photo-, solvent-, and ion-controlled multichromism of imidazolium-substituted diarylethenes Chem. Eur. J. 15 2009 1977 1984
26. S. Wang, W. Shen, Y. Feng, and H. Tian A multiple switching bisthienylethene and its photochromic fluorescent organogelator Chem. Commun. 2006 1497 1499
27. A.N. Shipway, and I. Willner Electronically transduced molecular mechanical and information functions on surfaces Acc. Chem. Res. 34 2001 421 432
28. X. Meng, W. Zhu, Q. Zhang, Y. Feng, W. Tan, and H. Tian Novel bisthienylethenes containing naphthalimide as the center ethene bridge: photochromism and solvatochromism for combined NOR and INHIBIT logic gates J. Phys. Chem. B 112 2008 15636 15645
29. B.L. Feringa, R.A. van Delden, N. Koumura, and E.M. Geertsema Chiroptical molecular switches Chem. Rev. 100 2000 1789 1816
30. G.B.K. Weiss Spiropyrans and spirooxazines for memories and switches Chem. Rev. 100 2000 1741 1754
31. G.M. Tsivgoulis, and J.-M. Lehn Photoswitched and functionalized oligothiophenes: synthesis and photochemical and electrochemical properties Chem. Eur. J. 2 1996 1399 1406
32. T.B. Norten, and N.R. Branda Photoregulation of fluorescence in a porphyrinic dithienylethene photochrome J. Am. Chem. Soc. 123 2001 1784 1785
33. S.-J. Lim, J. Seo, and S.Y. Park Photochromic switching of excited-state intramolecular proton-transfer (ESIPT) fluorescence: a unique route to high-contrast memory switching and nondestructive readout J. Am. Chem. Soc. 128 2006 14542 14547
34. J. Krnbratt, M. Hammarson, S. Li, H.L. Anderson, B. Albinsson, and J. Andrasson Photochromic supramolecular memory with nondestructive readout Angew. Chem. Int. Ed. 49 2010 1854 1857
35. T. Nakagawa, Y. Hasegawa, and T. Kawai Nondestructive luminescence intensity readout of a photochromic ianthanide(III) complex Chem. Commun. 2009 5630 5632
36. H. Seibold, and H. Port Mid-infrared recognition of the reversible photoswitching of fulgides Chem. Phys. Lett. 252 1996 135 140
37. F. Stellacci, C. Bertarelli, F. Toscano, M.C. Gallazzi, and G. Zerbi Diarylethene-based photochromic rewritable optical memories: on the possibility of reading in the mid-infrared Chem. Phys. Lett. 302 1999 563 570
38. K. Uchida, M. Saito, A. Murakami, S. Nakamura, and M. Irie Non-destructive readout of the photochromic reactions of diarylethene derivatives using infrared light Adv. Mater. 15 2003 121 125
39. N.P.M. Huck, W.F. Jager, B. de Lange, and B.L. Feringa Dynamic control and amplification of molecular chirality by circular polarized light Science 273 1996 1686 1688
40. D. Sud, T.B. Norsten, and N.R. Branda Photoswitching of stereoselectivity in catalysis using a copper dithienylethene complex Angew. Chem. Int. Ed. 44 2005 2019 2021
41. Y. Yokoyama, T. Shiozawa, Y. Tani, and T. Ubukata A unified strategy for exceptionally high diastereoselectivity in the photochemical ring closure of chiral diarylethenes Angew. Chem. Int. Ed. 48 2009 4521 4523
42. M. Irie, O. Miyatake, and K. Uchida Blocked photochromism of diarylethenes J. Am. Chem. Soc. 114 1992 8715 8716
43. S.-H. Kawai, S.L. Gilat, R. Ponsinet, and J.-M. Lehn A dual-mode molecular switching device: bisphenolic diarylethenes with integrated photochromic and electrochromic properties Chem. Eur. J. 1 1995 285 293
44. Y. Chen, D.X. Zeng, and M.G. Fan Synthesis and photochromic properties of functional diarylethene with a 2,5-dihydrothiophene bridging unit Org. Lett. 5 2003 1435 1437
45. E. Sada, H. Kumazawa, T. Amano, I. Kudo, and T. Kondo Absorption of carbon dioxide in aqueous solutions of sodium phenoxide Chem. Eng. J. 13 1977 41 44