Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.3.875

Synthesis of New Bicyclic Aziridines Containing Chalcone Analogs and Investigation of Their Photochromic Properties  

Besharati-Seidani, Tayebeh (Chemistry Department, Faculty of Science, University of Guilan)
Mahmoodi, Nosrat O. (Chemistry Department, Faculty of Science, University of Guilan)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.3, 2013 , pp. 875-883 More about this Journal
Abstract
Ten new derivatives of 1,3-diazabicyclo[3.1.0]hex-3-enes linked via ether linkage to chalcones were synthesized and characterized by UV, FT-IR, $^1H$ NMR and $^{13}C$ NMR spectral techniques. The spectra of all synthesized compounds, confirmed structure-photochromic behavior relationships (SPBR) both in solution or in solid state by irradiation under UV light at 254 nm. In other efforts for first time photochromic behavior of ketoaziridines has been investigated.
Keywords
Bicyclic aziridine; Chalcone; Ketoaziridine; Photochromism;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Pu, S.; Yang, T.; Chen, B.; Xu, J. Can. J. Chem. 2007, 85, 12.   DOI   ScienceOn
2 Choi, D. H.; Kim, J. H.; Ban, S. Y.; Kaihua, S. Dyes and Pigments 2003, 58, 105.   DOI   ScienceOn
3 Andréasson, J.; Karnbratt, J.; Hammarson, M.; Li, S.; Anderson, H. L.; Albinsson, B. Angew. Chem. Int. Ed. 2010, 49, 1854.   DOI   ScienceOn
4 Raymo, F. M.; Tomasulo, M. Chem. Eur. J. 2006, 12, 3186.   DOI   ScienceOn
5 Raymo, F. M.; Cusido, J.; Deniz, E. Eur. J. Org. Chem. 2009, 2031.
6 Facke, T.; Bruder, F.-K.; Hagen, R.; Rolle, T.; Weiser, M.-S. Angew. Chem. Int. Ed. 2011, 50, 4552.   DOI   ScienceOn
7 Leigh, D. A.; Kay, E. R.; Zerbetto, F. Angew. Chem. Int. Ed. 2007, 46, 72.   DOI   ScienceOn
8 Ikeda, K.; Uosaki, K. Chem. Eur. J. 2012, 18, 1564.   DOI   ScienceOn
9 Solomon, D. H.; Prime, E. L. Angew. Chem. Int. Ed. 2010, 49, 3726.   DOI   ScienceOn
10 Willner, I.; Willner, B. Adv. Mater. 1997, 9(4).
11 Yamaguchi, T.; Irie, M. Eur. J. Org. Chem. 2006, 3105.
12 Grzybowski, B. A.; Han, S.; Wei, Y.; Valente, C.; Forgan, R. S.; Gassensmith, J. J.; Smaldone, R. A.; Nakanishi, H.; Coskun, A.; Stoddart, J. F. Angew. Chem. Int. Ed. 2011, 50, 276.   DOI   ScienceOn
13 Matyjaszewski, K.; Lee, H. I.; Wu, W.; Oh, J. K.; Mueller, L.; Sherwood, G.; Peteanu, L.; Kowalewski, T. Angew. Chem. Int. Ed. 2007, 46, 2453.   DOI   ScienceOn
14 Irie, M.; Terao, F.; Morimoto, M. Angew. Chem. Int. Ed. 2012, 51, 901   DOI   ScienceOn
15 Yu, H.; Ikeda, T. Adv. Mater. 2011, 23, 2149.   DOI   ScienceOn
16 Yin, Y.; Ge, J. Angew. Chem. Int. Ed. 2011, 50, 1492.   DOI   ScienceOn
17 Pawar, R. P.; Sardaa, S. R.; Jadhavb, W. N.; Tekaleb, S. U.; Jadhavb, G. V.; Patilb, B. R.; Suryawanshib, G. S. Lett. Org. Chem. 2009, 6, 481.   DOI   ScienceOn
18 Ngaini, Z.; Abdul Rahman, N. I. Can. J. Chem. 2010, 88, 654.   DOI   ScienceOn
19 Nanjundan, S.; Selvamalar, C. S. J. Macromol. Sci. Pure. Appl. Chem. 2006, 43, 1189.   DOI   ScienceOn
20 Rami Reddy, A. V.; Subramanian, K.; Sesha Sainath, A. V. J. Appl. Polym. Sci. 1998, 70, 2111.   DOI
21 Nanjundan, S.; Balaji, R. J. Appl. Polym. Sci. 2002, 86, 1023.   DOI   ScienceOn
22 Seo, D.-S.; Hwang, J.-Y. J. Opt. Soc. Korea 2001, 5(1), 16.   DOI   ScienceOn
23 Seo, D.-S.; Hwang, J.-Y.; Hahn, E.-J.; Kim, J.-H. Trans. Electr. Electron. Mater 2000, 1(3).
24 Mahmoodi, N. O.; Kiyani, H. Bull. Korean Chem. Soc. 2004, 25(9), 1417.   DOI   ScienceOn
25 Mahmoodi, N. O.; Zanjanchi, M. A.; Kiyani, H. J. Chem. Res. 2004, 438.
26 Mahmoodi, N. O.; Yazdanbakhsh, M. R.; Kiyani, H.; Shrifzadeh, B. J. Chin. Chem. Soc. 2007, 54, 635.
27 Mahmoodi, N. O.; Kiyani, H.; Tabatabaeian, K.; Zanjanchi, M. A.; Arvand, M.; Sharifzadeh, B. Russ. J. Org. Chem. 2010, 46(6), 884.   DOI
28 Mahmoodi, N. O.; Kiyani, H.; Tabatabaeian, K.; Zanjanchi, M. A. J. Phys. Org. Chem. 2009, 22, 559.   DOI   ScienceOn
29 Mahmoodi, N. O.; Kiyani, H.; Tabatabaeian, K.; Zanjanchi, M. A. Mendeleev commun. 2009, 19, 203.   DOI   ScienceOn
30 Mahmoodi, N. O.; Tabatabaeian, K.; Kiyani, H. Helv. Chim. Acta 2012, 95(3), 536.   DOI   ScienceOn
31 Shen, K.; Han, J.; Wang, J.; Wang, G.; Li, Y.; Zhao, D. J. Appl. Polym. Sci. 2012, Doi: 10.1002/app.36419.
32 Mahmoodi, N. O.; Tabatabaeian, K.; Ghavidast, A. Chinese Chem. Lett. 2010, 21, 1199.   DOI   ScienceOn
33 Hopf, H.; Beck, C.; Desvergne, J. P.; Bouas-Laurent, H.; Jones, P. G.; Ernst, L. Beilstein J. Org. Chem. 2009, 5(20), 1, published 07 May 2009, doi:10.3762/bjoc.5.20.   DOI   ScienceOn
34 Kinashi, K.; Nakamura, S.; Imamura, M.; Ishidab, K.; Ueda, Y. J. Phys. Org. Chem. 2012, 25, 462.   DOI   ScienceOn
35 Hopf, H.; Greiving, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J. P.; Bouas-Laurent, H. Eur. J. Org. Chem. 2005, 558.
36 Hopf, H.; Greiving, H.; Beck, C.; Dix, I.; Jones, P. G.; Desvergne, J. P.; Bouas-Laurent, H. Eur. J. Org. Chem. 2005, 567.
37 Kannan, P.; Sakthivel, P. Polym. Int. 2005, 54, 1490.   DOI   ScienceOn
38 38. Chang, J. Y.; Nam, S. W.; Kang, S. H. Macromol. Res. 2007, 15(1), 74.   DOI   ScienceOn
39 Rehab, A. J. Macromol. Sci. Pure. Appl. Chem. 2005, 42, 327.   DOI   ScienceOn
40 Choi, D. H.; Shen, K.; Kim, J. H.; Kim, G. W.; Cho, M. J.; Lee, S. K. Macromol. Res. 2005, 13(3), 180.   DOI   ScienceOn
41 Yayli, N.; Ucuncu, O.; Yasar, A.; Gok, Y.; Kucuk, M.; Kolayli, S. Turk J. Chem. 2004, 28, 515.
42 Kim, J. D.; Choi, K. S.; Kim, H. W.; Kim, Y. B. Liq. Cryst. 2004, 31(5), 639.   DOI   ScienceOn
43 Choi, D. H.; Ban, S. Y.; Kaihua, S.; Kim, J. H. Mol. Cryst. Liq. Cryst. 2003, 406, 93.   DOI   ScienceOn
44 Song, D. M.; Jung, K. H.; Shin, D. M. Mol. Cryst. Liq. Cryst. 2002, 377, 117.   DOI
45 Anderson, H. L.; Frampton, M. J. Angew. Chem. Int. Ed. 2007, 46, 1028.   DOI   ScienceOn
46 Dimmock, J. R.; Kandepu, N. M.; Hetherington, M.; Quail, J. W.; Pugazhenthi, U.; Sudom, A. M.; Chamankhah, M.; Rose, P.; Pass, E.; Allen, T. M.; Halleran, S.; Szydlowski, J.; Mutus, B.; Tannous, M.; Manavathu, E. K.; Myers, T. G.; De Clercq, E.; Balzarini, J. J. Med. Chem. 1998, 41, 1014.   DOI   ScienceOn