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Synthesis and properties of 3-ethynylthiophene containing BODIPY derivatives
Reuben Warshawsky (1)
, Jason Vaal (2,*) , Priya Hewavitharanage (3) (1) Department of Chemistry, University of Southern Indiana, Evansville, Indiana 47712, USA
(2) Department of Chemistry, University of Southern Indiana, Evansville, Indiana 47712, USA
(3) Department of Chemistry, University of Southern Indiana, Evansville, Indiana 47712, USA
(*) Corresponding Author
Received: 01 Aug 2017, Accepted: 09 Sep 2017, Published: 31 Dec 2017
Abstract
Green, red and far-red emitting Borondipyrromethene (BODIPY) derivatives with 3-ethynylthiophene units at various positions around the BODIPY core were synthesized and their photophysical properties were studied. 3-Ethynylthiophene substitution at the 2,6 positions caused significant increase in Stokes shift while substitution at the 8 and 4,4’ positions had no effect. Photooxidation of 1,3-diphenylisobenzofuran (DPBF) in the presence of 3-ethynylthiophene substituted BODIPY derivatives confirmed singlet oxygen generation. 3-Ethynylthiophene substitution at the 2,6 positions is more effective in singlet oxygen generation compared to 4’4 substitutions. Substitution through phenyl group at the meso (8) position gave the lowest rate for singlet oxygen production. All 3-ethynylthiophene containing BODIPY derivatives were highly photo-stable under our experimental conditions.
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DOI: 10.5155/eurjchem.8.4.321-327.1634
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References
[1]. Ulrich, G.; Ziessel, R.; Harriman, A. Angew. Chem. Int. Ed. 2008, 47, 1184-1201.
https://doi.org/10.1002/anie.200702070
[2]. Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891-4932.
https://doi.org/10.1021/cr078381n
[3]. Chang, T. C.; Kuo, C. T.; Chiang, C. C.; Cheng, J. Y.; Yan, C. S.; Peck, K. Phys. Chem. 1999, 1, 3783-3787.
[4]. Giebler, K.; Griesser, H.; Göhringer, D.; Sabirov, T.; Richert, C. Eur. J. Org. Chem. 2010, 19, 3611-3620.
[5]. Goncalves, M. S. T. Chem. Rev. 2009, 109, 190-212.
https://doi.org/10.1021/cr0783840
[6]. Rostron, J. P.; Ulrich, G.; Retailleau, P.; Hamman, A.; Ziessel, R. New J. Chem. 2005, 29, 1241-1244.
https://doi.org/10.1039/b507585h
[7]. Khatchadourian, A.; Krumova, K.; Boridy, S.; Ngo, A. T. Biochemistry. 2009, 48, 5658-5668.
https://doi.org/10.1021/bi900402c
[8]. Jiao, L.; Yu, C.; Uppal, T.; Liu, M.; Li, Y.; Zhou, Y.; Hao, E.; Hu, X.; Vicente, G. H. Org. Biomol. Chem. 2010, 8, 2517-2519.
https://doi.org/10.1039/c001068e
[9]. Kang, H. C.; Haugland, R. P. U. S. Patent 5, 433, 896, July 18, 1995.
[10]. Rihn, S.; Retailleau, P.; Bugsaliewicz, N.; De Nicola, A.; Ziessel, R. Tetrahedron Lett. 2009, 50, 7008-7013.
https://doi.org/10.1016/j.tetlet.2009.09.163
[11]. Sobenina, L. N.; Vasil'tsov, A. M.; Petrova, O. V.; Petrushenko, K. B.; Ushakov, I. A.; Clavier, G.; Meallet-Renault, R.; Mikhaleva, A. I.; Trofimov, B. A. Org. Lett. 2011, 13, 2524-2527.
https://doi.org/10.1021/ol200360f
[12]. Poirel, A.; Nicola, A. D.; Ziesse, R. Org. Lett. 2012, 14, 5696-5699.
https://doi.org/10.1021/ol302710z
[13]. Hewavitharanage, P.; Nzeata, P.; Wiggins, J. Eur. J. Chem. 2012, 3, 13‐16.
https://doi.org/10.5155/eurjchem.3.1.13-16.543
[14]. Goze, C.; Ulrich, G.; Ziessel, R. J. Org. Chem. 2007, 72, 313-322.
https://doi.org/10.1021/jo060984w
[15]. Goze, C.; Ulrich, G.; Ziessel, R. Org. Lett. 2006, 8, 4445-4448.
https://doi.org/10.1021/ol061601j
[16]. Harriman, A.; Mallon, L. J.; Elliot, K. J.; Haefele, A.; Ulrich, G.; Ziessel, R. J. Am. Chem. Soc. 2009, 131, 13375-13386.
https://doi.org/10.1021/ja9038856
[17]. Chen, Y.; Zhao, J.; Guo, H.; Xie, L. J. Org. Chem. 2012, 77, 2192-2206.
https://doi.org/10.1021/jo202215x
[18]. Kaneza, N.; Zhang, J.; Haiying, L.; Archana, P. S.; Shan, Z.; Vasiliu, M.; Polansky, S. H.; Dixon, D. A.; Adams, R. E.; Schmehl, R. H. J. Phys. Chem. C. 2016, 120, 9068-9080.
https://doi.org/10.1021/acs.jpcc.6b01611
[19]. Mirloup, A.; Leclerc, N.; Rihn, S.; Bura, T.; Bechara, R.; Hebraud, A.; Leveque, P.; Heiser, T.; Ziessel, R. New J. Chem. 2014, 38, 3644-3653.
https://doi.org/10.1039/C4NJ00294F
[20]. Shimizu, S.; Iino, T.; Saeki, A.; Seki, S.; Kobayashi, N. Chem. Eur. J. 2015, 21, 2893-2904.
https://doi.org/10.1002/chem.201405761
[21]. Cortizo-Lacalle, D.; Howells, C. T.; Pandey, U. K.; Cameron, J.; Findlay, N. J.; Inigo, A. R.; Tuttle, T.; Skabara, P. J.; Samuel, I. D. W. Beilstein J. Org. Chem. 2014, 10, 2683-2695.
https://doi.org/10.3762/bjoc.10.283
[22]. Poirel, A.; De Nicola, A.; Ziessel, R. Org. Lett. 2012, 14, 5696-5699.
https://doi.org/10.1021/ol302710z
[23]. Wu, Y.; Klaubert, D. H.; Kang, H. C.; Zhang, Y. Z. U. S. Patent 6 005 113, 1999.
[24]. Yogo, T.; Urano, Y.; Ishitsuka, Y.; Maniwa, F.; Nagano, T. J. Am. Chem. Soc. 2005, 127, 12162-12163.
https://doi.org/10.1021/ja0528533
[25]. Caishun, Z.; Jianzhang, Z.; Shuo, W., Zilong, W.; Wanhua, W.; Jie, M.; Song, G.; Ling, H. J. Am. Chem. Soc. 2013, 135, 10566-10578.
https://doi.org/10.1021/ja405170j
[26]. He, H.; Lo, P. C.; Yeung, S. L.; Fong, W. P.; Ng, D. K. P. J. Med. Chem. 2011, 54, 3097-3102.
https://doi.org/10.1021/jm101637g
[27]. He, H.; Lo, P. C.; Yeung, S. L.; Fong, W. P.; Ng, D. K. P. Chem. Commun. 2011, 47, 4748-4750.
https://doi.org/10.1039/c1cc10727e
[28]. Wu, W; Guo, H; Wu, W.; Ji, S.; Zhao, J. J. Org. Chem. 2011, 76, 7056-7064.
https://doi.org/10.1021/jo200990y
[29]. Awuah, S. G.; Polreis, J.; Biradar, v.; You, Y. Org. Lett. 2011, 15, 3884-3887.
https://doi.org/10.1021/ol2014076
[30]. Topel, S. D.; Cin, G. T.; Akkaya, E. U. Chem. Commun. 2014, 50, 8896-8899.
https://doi.org/10.1039/C4CC03387F
[31]. Umezawa, K.; Matsui, A.; Nakamura, Y.; Citterio, D.; Suzuki, K. Chem. Eur. J. 2009, 15, 1096-1106.
https://doi.org/10.1002/chem.200801906
[32]. Jiang, N.; Fan, J.; Liu, T.; Cao, J.; Qiao, B.; Wang, J.; Gao, P.; Peng, X. Chem. Commun. 2013, 49, 10620-10622.
https://doi.org/10.1039/c3cc46143b
[33]. Ji, S.; Ge, J.; Escudero, D.; Wang, Z.; Zhao, J.; Jacquemin, D. J. Org. Chem. 2015, 80, 5958-5963.
https://doi.org/10.1021/acs.joc.5b00691
[34]. Vincent, M.; Beabout, E.; Bennett, R. Hewavitharanage, P. Tetrahedron Lett. 2013, 54: 2050-2054.
https://doi.org/10.1016/j.tetlet.2013.01.128
[35]. Niu, S.; Ulrich, G.; Retailleau, P.; Ziessel, R. Org. Lett. 2011, 13, 4996-4999.
https://doi.org/10.1021/ol201600s
[36]. Singh-Rachford, T. N.; Haefele, A.; Ziessel, R.; Castellano, F. N. J. Am. Chem. Soc. 2008, 130, 16164-16165.
https://doi.org/10.1021/ja807056a
[37]. Coskun, A.; Yilmaz, M. D.; Akkaya, E. U. Org. Lett. 2007, 9, 607-609.
https://doi.org/10.1021/ol062867t
[38]. Lissi, E. A.; Encinas, M. V.; Lemp, E.; Rubio, M. A. Chem. Rev. 1993, 93, 699-723.
https://doi.org/10.1021/cr00018a004
[39]. Adarsh, N.; Avirah, R. R.; Ramaiah, D. Org. Lett. 2010, 12, 5720-5723.
https://doi.org/10.1021/ol102562k
[40]. Kim, S.; Ohulchanskyy, T. Y.; Baev, A.; Prasad, P. N. J. Mater. Chem. 2009, 19, 3181-3188.
https://doi.org/10.1039/b813396d
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