European Journal of Chemistry 2017, 8(4), 321-327 | doi: https://doi.org/10.5155/eurjchem.8.4.321-327.1634 | Get rights and content






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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 | Revised: 08 Sep 2017 | Accepted: 09 Sep 2017 | Published: 31 Dec 2017 | Issue Date: December 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.


Keywords


BODIPY; Thiophene; Stokes shift; Fluorescence; Singlet oxygen; Photodynamic therapy

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DOI: 10.5155/eurjchem.8.4.321-327.1634

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Funding information


The University of Southern Indiana Endeavor Award for Research & Creativity (Project no: 17786-01000) and by the Lilly Summer Student Research Fellowship (Project no: 25075-01820)

Citations

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[1]. Priyadarshine Hewavitharanage, Reuben Warshawsky, Sergiy V. Rosokha, Jason Vaal, Kelsey Stickler, Dmitriy Bachynsky, Neil Jairath
Efficient energy transfer in phenyl-ethynyl-linked asymmetric BODIPY dimers
Tetrahedron  76(42), 131515, 2020
DOI: 10.1016/j.tet.2020.131515
/

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

How to cite


Warshawsky, R.; Vaal, J.; Hewavitharanage, P. Eur. J. Chem. 2017, 8(4), 321-327. doi:10.5155/eurjchem.8.4.321-327.1634
Warshawsky, R.; Vaal, J.; Hewavitharanage, P. Synthesis and properties of 3-ethynylthiophene containing BODIPY derivatives. Eur. J. Chem. 2017, 8(4), 321-327. doi:10.5155/eurjchem.8.4.321-327.1634
Warshawsky, R., Vaal, J., & Hewavitharanage, P. (2017). Synthesis and properties of 3-ethynylthiophene containing BODIPY derivatives. European Journal of Chemistry, 8(4), 321-327. doi:10.5155/eurjchem.8.4.321-327.1634
Warshawsky, Reuben, Jason Vaal, & Priya Hewavitharanage. "Synthesis and properties of 3-ethynylthiophene containing BODIPY derivatives." European Journal of Chemistry [Online], 8.4 (2017): 321-327. Web. 22 Oct. 2020
Warshawsky, Reuben, Vaal, Jason, AND Hewavitharanage, Priya. "Synthesis and properties of 3-ethynylthiophene containing BODIPY derivatives" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

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DOI Link: https://doi.org/10.5155/eurjchem.8.4.321-327.1634

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