Reversible photochromic system based on rhodamine B salicylaldehyde hydrazone metal complex

Journal of the American Chemical Society

Volumn 136, Issue 4, 2014, Pages 1643-1649

  Li, Kai ^a   Xiang, Yu ^a   Wang, Xiaoyan ^a   Li, Ji ^a   Hu, Rongrong ^b   Tong, Aijun ^a   Tang, Ben Zhong ^b  

^a TSINGHUA UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL SUBSTITUTION; LARGE ABSORPTION COEFFICIENT; LIGHT CONVERSION; LONG-WAVELENGTH ABSORPTION; PHOTO-CHROMIC MATERIALS; PHOTOCHROMIC MOLECULES; PHOTOCHROMIC SYSTEMS; THERMAL BLEACHING;

BLEACHING; CHROMOGENICS; CHROMOPHORES; CLEANING; FATIGUE OF MATERIALS; METAL COMPLEXES; METAL IONS; MOLECULES; SYNTHESIS (CHEMICAL);

PHOTOCHROMISM;

HYDRAZONE DERIVATIVE; METAL COMPLEX; METAL ION; POLOXAMER; RHODAMINE B; RHODAMINE B SALICYLALDEHYDE HYDRAZONE METAL COMPLEX; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; BLEACHING; CHEMICAL STRUCTURE; CHROMATOPHORE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DIPOLE; FLUORESCENCE; PHOTOCHEMISTRY; PHOTOCHROMIC SYSTEM; SYNTHESIS; TAUTOMER; ULTRAVIOLET IRRADIATION;

ALDEHYDES; HYDRAZONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHOTOCHEMICAL PROCESSES; QUANTUM THEORY; RHODAMINES; ULTRAVIOLET RAYS; ZINC;

EID: 84893516277     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja411689w     Document Type: Article

References (60)

1. Raymo, F. M.; Tomasulo, M. Chem. Soc. Rev. 2005, 34, 327
2. Yildiz, I.; Deniz, E.; Raymo, F. M. Chem. Soc. Rev. 2009, 38, 1859
3. Liu, D.; Chen, W.; Sun, K.; Deng, K.; Zhang, W.; Wang, Z.; Jiang, X. Angew. Chem., Int. Ed. 2011, 50, 4103
4. Dong, H.; Zhu, H.; Meng, Q.; Gong, X.; Hu, W. Chem. Soc. Rev. 2012, 41, 1754
5. Tsujioka, T.; Irie, M. J. Photochem. Photobiol., C 2010, 11, 1
6. Herder, M.; Utecht, M.; Manicke, N.; Grubert, L.; Pätzel, M.; Saalfrank, P.; Hecht, S. Chem. Sci. 2013, 4, 1028
7. Roldan, D.; Kaliginedi, V.; Cobo, S.; Kolivoska, V.; Bucher, C.; Hong, W.; Royal, G.; Wandlowski, T. J. Am. Chem. Soc. 2013, 135, 5974
8. Wang, F.; Liu, X.; Willner, I. Adv. Mater. 2013, 25, 349
9. Yagai, S.; Kitamura, A. Chem. Soc. Rev. 2008, 37, 1520
10. Chen, S.; Chen, L.-J.; Yang, H.-B.; Tian, H.; Zhu, W. J. Am. Chem. Soc. 2012, 134, 13596
11. Gopal, A.; Hifsudheen, M.; Furumi, S.; Takeuchi, M.; Ajayaghosh, A. Angew. Chem., Int. Ed. 2012, 124, 10657
12. Cui, J.; Gropeanu, R. A.; Stevens, D. R.; Rettig, J.; Campo, A. J. Am. Chem. Soc. 2012, 134, 7733
13. Natali, M.; Giordani, S. Chem. Soc. Rev. 2012, 41, 4010
14. Tong, R.; Hemmati, H. D.; Langer, R.; Kohane, D. S. J. Am. Chem. Soc. 2012, 134, 8848
15. Vantomme, G.; Lehn, J. M. Angew. Chem., Int. Ed. 2013, 125, 4032
16. Blanco-Lomas, M.; Samanta, S.; Campos, P. J.; Woolley, G. A.; Sampedro, D. J. Am. Chem. Soc. 2012, 134, 6960
17. Szymanski, W.; Beierle, J. M.; Kistemaker, H. A.; Velema, W. A.; Feringa, B. L. Chem. Rev. 2013, 113, 6114
18. Carroll, G. T.; Pollard, M. M.; van Delden, R.; Feringa, B. L. Chem. Sci. 2010, 1, 97
19. Marchi, E.; Baroncini, M.; Bergamini, G.; Van Heyst, J.; Vögtle, F.; Ceroni, P. J. Am. Chem. Soc. 2012, 134, 15277
20. Han, M.; Michel, R.; He, B.; Chen, Y. S.; Stalke, D.; John, M.; Clever, G. H. Angew. Chem., Int. Ed. 2013, 52, 1319
21. Zhang, J.; Zou, Q.; Tian, H. Adv. Mater. 2013, 25, 378
22. Wang, Z. Y.; Todd, E. K.; Meng, X. S.; Gao, J. P. J. Am. Chem. Soc. 2005, 127, 11552
23. Beharry, A. A.; Woolley, G. A. Chem. Soc. Rev. 2011, 40, 4422
24. Stein, M.; Middendorp, S. J.; Carta, V.; Pejo, E.; Raines, D. E.; Forman, S. A.; Sigel, E.; Trauner, D. Angew. Chem., Int. Ed. 2012, 51, 10500
25. Bleger, D.; Schwarz, J.; Brouwer, A. M.; Hecht, S. J. Am. Chem. Soc. 2012, 134, 20597
26. Minkin, V. I. Chem. Rev. 2004, 104, 2751
27. Wen, G.; Yan, J.; Zhou, Y.; Zhang, D.; Mao, L.; Zhu, D. Chem. Commun. 2006, 28, 3016
28. Niazov, T.; Shlyahovsky, B.; Willner, I. J. Am. Chem. Soc. 2007, 129, 6374
29. Balogh, D.; Tel-Vered, R.; Freeman, R.; Willner, I. J. Am. Chem. Soc. 2011, 133, 6533
30. Leung, D.; Kang, S. O.; Anslyn, E. V. Chem. Soc. Rev. 2012, 41, 448
31. Xie, X.; Mistlberger, G. N.; Bakker, E. J. Am. Chem. Soc. 2012, 134, 16929
32. Tian, H.; Yang, S. Chem. Soc. Rev. 2004, 33, 85
33. Zhu, W.; Yang, Y.; Métivier, R.; Zhang, Q.; Guillot, R.; Xie, Y.; Tian, H.; Nakatani, K. Angew. Chem., Int. Ed. 2011, 50, 10986
34. Perrier, A. l.; Maurel, F. O.; Jacquemin, D. Acc. Chem. Res. 2012, 45, 1173
35. Fukaminato, T.; Doi, T.; Tamaoki, N.; Okuno, K.; Ishibashi, Y.; Miyasaka, H.; Irie, M. J. Am. Chem. Soc. 2011, 133, 4984
36. Berberich, M.; Natali, M.; Spenst, P.; Chiorboli, C.; Scandola, F.; Würthner, F. Chem.-Eur. J. 2012, 18, 13651
37. Cheng, H.-B.; Zhang, H.-Y.; Liu, Y. J. Am. Chem. Soc. 2013, 135, 10190
38. Yang, Y.; Hughes, R. P.; Aprahamian, I. J. Am. Chem. Soc. 2012, 134, 15221
39. Iida, A.; Saito, S.; Sasamori, T.; Yamaguchi, S. Angew. Chem., Int. Ed. 2013, 52, 3760
40. Moorthy, J. N.; Mandal, S.; Mukhopadhyay, A.; Samanta, S. J. Am. Chem. Soc. 2013, 135, 6872
41. Nakai, H.; Kitagawa, K.; Nakamori, H.; Tokunaga, T.; Matsumoto, T.; Nozaki, K.; Ogo, S. Angew. Chem., Int. Ed. 2013, 52, 1
42. Song, L.; Yang, Y.; Zhang, Q.; Tian, H.; Zhu, W. J. Phys. Chem. B 2011, 115, 14648
43. Yang, Y.; Xie, Y.; Zhang, Q.; Nakatani, K.; Tian, H.; Zhu, W. Chem.-Eur. J. 2012, 18, 11685
44. Shi, W.; Ma, H. Chem. Commun. 2012, 48, 8732
45. Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Chem. Rev. 2013, 113, 192
46. Yang, Y.; Seidlits, S. K.; Adams, M. M.; Lynch, V. M.; Schmidt, C. E.; Anslyn, E. V.; Shear, J. B. J. Am. Chem. Soc. 2010, 132, 13114
47. Knauer, K. H.; Gleiter, R. Angew. Chem. 1977, 89, 116
48. Willwohl, H.; Wolfrum, J.; Gleiter, R. Laser Chem. 1989, 10, 63
49. Fölling, J.; Belov, V.; Kunetsky, R.; Medda, R.; Schönle, A.; Egner, A.; Eggeling, C.; Bossi, M.; Hell, S. E. W. Angew. Chem., Int. Ed. 2007, 46, 6266
50. Belov, V. N.; Bossi, M. L.; Fölling, J.; Boyarskiy, V. P.; Hell, S. W. Chem.-Eur. J. 2009, 15, 10762
51. Wu, L.; Dai, Y.; Marriott, G. Org. Lett. 2011, 13, 2018
52. Schäfer, C. G.; Gallei, M.; Zahn, J.; Engelhardt, J.; Hellmann, G. P.; Rehahn, M. Chem. Mater. 2013, 25, 2309
53. Dürr, H.; Bouas-Laurent, H. Photochromism: Molecules and Systems; Elsevier: Amsterdam, 1990.
54. Hadjoudis, E.; Mavridis, I. M. Chem. Soc. Rev. 2004, 33, 579
55. Li, N.; Tang, W.; Xiang, Y.; Tong, A.; Jin, P.; Ju, Y. Luminescence 2010, 25, 445
56. Meriwether, L.; Breitner, E.; Sloan, C. J. Am. Chem. Soc. 1965, 87, 4441
57. Fang, X.; Bando, Y.; Gautam, U. K.; Zhai, T.; Zeng, H.; Xu, X.; Liao, M.; Golberg, D. Crit. Rev. Solid State Mater. Sci. 2009, 34, 190
58. Fang, X.; Bando, Y.; Liao, M.; Gautam, U. K.; Zhi, C.; Dierre, B.; Liu, B.; Zhai, T.; Sekiguchi, T.; Koide, Y. Adv. Mater. 2009, 21, 2034
59. Fang, X.; Bando, Y.; Liao, M.; Zhai, T.; Gautam, U. K.; Li, L.; Koide, Y.; Golberg, D. Adv. Funct. Mater. 2010, 20, 500
60. World Health Organization. Ultraviolet radiation and theINTERSUN Programme. (2010. Available at http://www.who.int/uv/en/.