氟硼二异吲哚类化合物的合成及光学性能表征
收稿日期: 2014-01-15
修回日期: 2014-02-19
网络出版日期: 2014-03-13
基金资助
国家自然科学基金(No.81102314)、上海市自然科学基金(No.11ZR1400300)和高等学校博士学科点专项科研基金(No.20120074120008)资助项目.
Synthesis of Boron Diisoindolmethene Compounds and Spectral Properties
Received date: 2014-01-15
Revised date: 2014-02-19
Online published: 2014-03-13
Supported by
Project supported by the National Natural Science Fundation of Chnia (No. 81102314), the Science and Technology Commission of Shanghai Municipality (No. 11ZR1400300) and the Specialized Research Fund for the Doctoral Program of Higher Education (No. 20120074120008).
杨晓霞 , 林智星 , 蔺卉 , 蔡良珍 , 陶晓春 . 氟硼二异吲哚类化合物的合成及光学性能表征[J]. 有机化学, 2014 , 34(7) : 1429 -1436 . DOI: 10.6023/cjoc201401026
The new boron diisoindolmethene compounds were synthesized from ethyl benzoate and 1-phenylethanone, and characterized by 1H NMR, HRMS and IR. These compounds exhibited the long UV-absorption and fluorescence emission wavelength. The effects of substituents on the molar extinction coefficient, fluorescence quantum yield and singlet oxygen yield were easily noticed, methoxy substituted compound 6b and CF3 substituted compound 6f showed the higher molar extinction coefficient than other halogen substituted compounds, and compound 6e containing Br substituent exhibited the higher singlet oxygen yield and the lower fluorescence quantum yield than other compounds.
Key words: boron diisoindolmethene; synthesis; fluorescence; UV-Vis; singlet oxygen
[1] Burghart, A.; Kim, H. J.; Welch, M. B.; Thoresen, L. H.; Reibenspies, J.; Burgess, K.; Bergstrom, F.; Johansson, L. B. A. J. Org. Chem. 1999, 64, 7813.
[2] Yamada, K.; Toyota, T.; Takakura, K.; Ishimaru, M.; Sugawara, T.; New J. Chem. 2001, 25, 667
[3] Atilgan, S.; Ekmekci, Z.; Dogan, A. L.; Guc, D. Akkaya, E. U. Chem. Commun. 2006, 4398
[4] Gorman, A.; Killoran, J.; O'Shea, C.; Kenna, T.; Gallagher, W. M.; O'Shea, D. F. J. Am. Chem. Soc. 2004, 126, 10619
[5] Zhao, W. L.; Carreira, E. M. Chem. Eur. J. 2006, 12, 7254
[6] Moriarty, R. M.; Berghuid, N. A. Synthesis 1993, 318
[7] Katritzky, A. R; Harris, P. A.; Kotali, A. J. Org. Chem. 1991, 56, 5049
[8] Maekawa, E.; Suzuki, Y.; Sugiyama, S. Chem. Ber. 1968, 101, 847
[9] (a) Yuster, P.; Weissman, S. I. J. Chem. Phys. 1949, 17, 1182.
(b) McClure, D. S. J. Chem. Phys. 1949, 17, 905
[10] Lim, S. H.; Thivierge, C.; Nowak-Sliwinska, P.; Han, J. Y. Bergh, H.; Wagnieres, G.; Burgess, K.; Lee, H. B. J. Med. Chem. 2010, 53, 2865.
[11] Awuah, S. G.; You, Y. RSC Adv. 2012, 2, 11169
[12] Kamkaew, A.; Lim, S. H.; Lee, H. B.; Kiew, L. V.; Chung, L. Y.; Burgess, K. Chem. Soc. Rev. 2013, 42, 77
[13] Altalbawy, F. M. A.; Mohamed, G. G.; Mohamed, M. I. A. Asian J. Chem. 2010, 22, 7291.
[14] Kaushik, D.; Khan, S. A.; Chawla, G. Eur. J. Med. Chem. 2010, 45(9), 3960.
[15] Saha, A.; Kumar, R.; Kumar, R.; Devakumar, C. Indian J. Chem. 2010, 49B, 526.
[16] Horwitz, J. P.; Grakauskas, V. A. J. Org. Chem. 1954, 19, 194.
[17] Yagupol'skii, L. M.; Gruz, B. E. Ukr. Khem. Zh. 1957, 23, 634.
[18] Kotali, A.; Tsoungas, P. G. Tetrahedron Lett. 1987, 28(37), 4321
[19] Kang, H. C.; Haugland, R. P. US 5433896, 1995[Chem. Abstr. 1995, 123, 202039].
[20] Umezawa, K.; Matsui, A.; Nakamura, Y.; Citterio, D.; Suzuki, K. Chem. Eur. J. 2008, 15, 1096.
[21] Abimbola, O.; David, M.; Tebello, N. J. J. Mol. Struct. 2003, 650, 131.
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