European Journal of Chemistry 2012, 3(1), 13-16 | doi: | Get rights and content


Synthesis of an E-BODIPY based fluorescent Co-polymer containing organoboron quinolate units

Priya Hewavitharanage (1,*) , Prince Nzeata (2) , Jeffrey Wiggins (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) School of Polymers and High Performance Materials, University of Southern Mississippi, Hattiesburg, Mississippi, 39406, USA
(*) Corresponding Author

Received: 10 Nov 2011 | Revised: 04 Jan 2012 | Accepted: 04 Jan 2012 | Published: 31 Mar 2012 | Issue Date: March 2012


A novel fluorescent co-polymer with an organoboron quinolate and an E-BODIPY (BODIPY: 4,4-difluoro-4-bora-3a-4a-diaza-s-indacene) moiety was synthesized with the aim of producing a donor-acceptor polymeric system where the organoboron quinolate acts as the donor and the E-BODIPY moiety is the acceptor. The polymer has three prominent absorption bands: 264 nm (corresponding to the organoboron quinolate), 397 nm (corresponding to the organoboron quinolate and BODIPY) and 516 nm (corresponding to the E-BODIPY moiety). Excitation of the organoboron quinolate at 264 nm resulted in emission at 525 nm, giving a 261 nm Stokes shift. Energy transfer from the donor (organoboron quinolate) unit to the acceptor (BODIPY) explains the origin of this large Stokes shift.



BODIPY; Stokes shift; Fluorescence; Donor-acceptor; Energy transfer; Organoboron quinolate

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DOI: 10.5155/eurjchem.3.1.13-16.543

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Funding information

Science and Engineering Research Grant Award of University of the Southern Indiana (Project No: 17228-01780), Faculty Research and Creative Work Award of the University of Southern Indiana (Project No: 17271-01780) and the Indiana Academy of Science (Proj



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DOI: 10.1039/c4cc02706j

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[1]. Rao, Y. L.; Wang, S. Inorg. Chem. 2011, 50, 12263-12274.

[2]. Wang, S. Coord. Chem. Rev. 2001, 215, 79-98.

[3]. Entwistle, C. D.; Marder, T. B. Angew. Chem, Int. Ed. 2002, 41, 2927-2931.<2927::AID-ANIE2927>3.0.CO;2-L

[4]. Entwistle, C. D.; Marder, T. B. Chem. Mater. 2004, 16, 4574-4585.

[5]. Qin, Y.; Kiburu, I.; Shah, S.; Jakle, F. Org. Lett. 2006, 8, 5227-5230.

[6]. Qin, Y.; Pagba, C.; Piotrowiak, P.; Jakle, F. J. Am. Chem. Soc. 2004, 126, 7015-7018.

[7]. Galbraith, E.; James, T. D. Chem. Soc. Rev. 2010, 39, 3831-3842.

[8]. Zhang, G.; Palmer, G. M.; Dewhirst, M. W.; Fraser, C. L. Nat. Mater. 2009, 8, 747-751.
PMid:19668206 PMCid:2846459

[9]. Hapuarachchige, S.; Montano, G.; Ramesh, C.; Rodriguez, D.; Henson, L. H.; Williams, C. C.; Kadavakkollu, S.; Johnson, D. L.; Shuster, C. B.; Arterburn, J. B. J. Am. Chem. Soc. 2011, 133, 6780-6790.

[10]. Benstead, M.; Mehl, G. L.; Boyle, R. W. Tetrahedron 2011, 67, 3573-3601.

[11]. Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891-4932.

[12]. Wood, T. E.; Thompson, A. Chem. Rev. 2007, 107, 1831-1861.

[13]. Haugland, R. P. The Handbook. A Guide to Fluorescent Probes and Labeling Technologies, 10th ed., Molecular Probes, Inc., Eugene, Oregon, USA, 2005.

[14]. Zhao, Y.; Zhang, Y.; Lv, X.; Liu. Y.; Chen, M.; Wang, P.; Liu, J.; Guo, W. J. Mater. Chem. 2011, 21, 13168-13171.

[15]. Ulrich, G.; Goeb, S.; De Nicola, A.; Retailleau, P.; Ziessel, R. J. Org. Chem. 2011, 76, 4489-4505.

[16]. Hablot, D.; Retailleau, P.; Ziessel, R. Chem. Eur. J. 2010, 16, 13346-13351.

[17]. Ziessel, R.; Ulrich, G.; Olivier, J. H.; Bura, T.; Sutter, A. Chem. Comm. 2010, 46, 7978-7980.

[18]. Rachford, A. A.; Ziessel, R.; Bura, T.; Retailleau, P.; Castellano, F. N. Inorg. Chem. 2010, 49, 3730-3736.

[19]. Goze, C.; Ulrich, G.; Ziessel, R. J. Org. Chem. 2007, 72, 313-322.

[20]. Warnan, J.; Buchet, F.; Pellegrin, Y.; Blart, E.; Odobel, F. Org. Lett. 2011, 13, 3944-3947.

[21]. Kim, B.; Ma, B.; Donuru, V. R.; Liu, H.; Frechet, J. M. J. Chem. Comm. 2010, 46, 4148-4150.

[22]. McDonagh, C.; Burke, C. S; MacCraith, B. D. Chem. Rev. 2008, 108, 400-422.

[23]. Fan, F. J.; Zhang, Y.; Murphy, C. B.; Angell, S. E.; Parker, M. F. L.; Flynn, B. R.; Jones, W. E. Coord. Chem. Rev. 2009, 253, 401-422.

[24]. He, H.; Lo, P. C.; Yeung, S. L.; Fong, W. P.; Ng, D. K. P. Chem. Commun. 2011, 47, 4748-4750.

[25]. Lim, S. H.; Thivierge, C.; Nowak-Sliwinska, P.; Han, J.; Van Den Bergh, H.; Wagniares, G.; Burgess, K.; Lee, H. B. J. Med. Chem. 2010, 53, 2865-2874.

[26]. Yogo, T.; Urano, Y.; Ishitsuka, Y.; Maniwa, F.; Nagano, T. J. Am. Chem. Soc. 2005, 127, 12162-12163.

[27]. Yoshii, R.; Nagai, A.; Chujo, Y. J. Polym. Sci, Part A: Polym. Chem. 2010, 48, 5348-5356.

[28]. Donuru, V. R.; Zhu, S.; Green, S.; Liu, H. Polymer 2010, 51, 5359-5368.

[29]. Donuru, V. R.; Vegesna, G. K.; Velayudham, S.; Green, S; Liu, H. Chem. Mater. 2009, 21, 2130-2138.

[30]. Goze, C.; Ulrich, G.; Ziessel, R. Org. Lett. 2006, 8, 4445-4448.

[31]. Nagai, A.; Miyake, J.; Kokado, K.; Nagata, Y.; Chujo, Y. J. Am. Chem. Soc. 2008, 130, 15276-15287.

[32]. Nagata, Y.; Chujo, Y. Macromolecules 2007, 40, 6-8.

[33]. Nagata, Y.; Otaka, H.; Chujo, Y. Macromolecules 2008, 41, 737-740.

[34]. Tokoro, Y.; Nagai, A.; Kokado, K.; Chujo, Y. Macromolecules 2009, 42, 2988-2993.

[35]. Tokoro, Y.; Nagai, A.; Chujo, Y. Macromolecules 2010, 43, 6229-6233.

[36]. Toele, P.; Zhang, H.; Trieflinger, C.; Daub, J.; Glasbeek, M. Chem. Phys. Lett. 2003, 368, 66-75.

[37]. Casey, K. G.; Quitevis, E. L. J. Phys. Chem. 1998, 92, 6590-6594.

[38]. Hamai, S.; Hirayama, F. J. Phys. Chem. 1983, 87, 83-89.

How to cite

Hewavitharanage, P.; Nzeata, P.; Wiggins, J. Eur. J. Chem. 2012, 3(1), 13-16. doi:10.5155/eurjchem.3.1.13-16.543
Hewavitharanage, P.; Nzeata, P.; Wiggins, J. Synthesis of an E-BODIPY based fluorescent Co-polymer containing organoboron quinolate units. Eur. J. Chem. 2012, 3(1), 13-16. doi:10.5155/eurjchem.3.1.13-16.543
Hewavitharanage, P., Nzeata, P., & Wiggins, J. (2012). Synthesis of an E-BODIPY based fluorescent Co-polymer containing organoboron quinolate units. European Journal of Chemistry, 3(1), 13-16. doi:10.5155/eurjchem.3.1.13-16.543
Hewavitharanage, Priya, Prince Nzeata, & Jeffrey Wiggins. "Synthesis of an E-BODIPY based fluorescent Co-polymer containing organoboron quinolate units." European Journal of Chemistry [Online], 3.1 (2012): 13-16. Web. 7 Jul. 2020
Hewavitharanage, Priya, Nzeata, Prince, AND Wiggins, Jeffrey. "Synthesis of an E-BODIPY based fluorescent Co-polymer containing organoboron quinolate units" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

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