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

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.8.4.321-327.1634

Links for Article


| | | | | | |

| | | | | | |

| | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1274 times | icon graph PDF Article downloaded 356 times

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

/


[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
/

[2]. Bruno Hori Barboza, Orisson Ponce Gomes, Augusto Batagin-Neto
Polythiophene derivatives as chemical sensors: a DFT study on the influence of side groups
Journal of Molecular Modeling  27(1), , 2021
DOI: 10.1007/s00894-020-04632-w
/

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. 12 Apr. 2021
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)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



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

CrossRef | Scilit | GrowKudos | Researchgate | Publons | Microsoft | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)




© Copyright 2010 - 2021 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.