New Fluorene-Based Fluorescent Probe with Efficient Two-Photon Absorption

Authors

  • M. V. Bondar Institute of Physics
  • O. V. Przhonska Institute of Physics
  • O. D. Kachkovsky Insitute of Organic Chemistry
  • A. Frazer Department of Chemistry, University of Central Florida
  • A. R. Morales Department of Chemistry, University of Central Florida
  • K. D. Belfield Department of Chemistry, University of Central Florida

DOI:

https://doi.org/10.15407/ujpe58.08.0748

Keywords:

two-photon absorption, fluorene, Z-scan method

Abstract

The synthesis, linear photophysical characterization, and two-photon absorption (2PA) properties of new fluorene derivative 3,30-(pyridine-2,6-diyl)bis(1-(7-(diphenylamino)-9,9-dihexyl-9H-fluoren-2-yl)propane-1,3-dione) (1) have been presented. The steady-state absorption, fluorescence and excitation anisotropy spectra along with the fluorescence decay kinetics of 1 are obtained in the solvents of different polarities at room temperature with respect to its potential application in bioimaging. The analysis of linear photophysical properties revealed a complicated nature of the main one-photon absorption band of 1, and the strong solvatochromic effect in steady-state fluorescence spectra is observed. The degenerate 2PA spectrum of 1 is measured in the spectral range 570–970 nm with the use of the open aperture Z-scan method under the 1-kHz femtosecond excitation, and the maximum values of two-photon action cross sections ~(100–130) GM are obtained. The nature of the linear absorption and the 2PA bands is analyzed by quantum chemical methods using a Gaussian program package.

References

<ol>

<li> Z.S. An, S.A. Odom, R.F. Kelley, C. Huang, X. Zhang, S. Barlow, L.A. Padilha, J. Fu, S. Webster, D.J. Hagan, E.W. Van Stryland, S.M.R. Wasielewski, and S.R. Marder, J. Phys. Chem. A 113, 5585 (2009).
&nbsp;<a href="https://doi.org/10.1021/jp900152r">https://doi.org/10.1021/jp900152r</a>
</li>
<li> M. Rumi, S.J.K. Pond, T. Meyer-Friedrichsen, Q. Zhang, M. Bishop, Y. Zhang, S. Barlow, S.R. Marder, and J.W. Perry, J. Phys. Chem. C 112, 8061 (2008).
&nbsp;<a href="https://doi.org/10.1021/jp710682z">https://doi.org/10.1021/jp710682z</a>
</li>
<li> S.A. Odom, S. Webster, L.A. Padilha, D. Peceli, H. Hu, G. Nootz, S.J. Chung, S. Ohira, J.D. Matichak, O.V. Przhonska, A.D. Kachkovski, S. Barlow, J.L. Bredas, H.L. Anderson, D.J. Hagan, E.W. Van Stryland, and S.R. Marder, J. Am. Chem. Soc. 131, 7510 (2009).
&nbsp;<a href="https://doi.org/10.1021/ja901244e">https://doi.org/10.1021/ja901244e</a>
</li>
<li> M. Balu, L.A. Padilha, D.J. Hagan, E.W. Van Stryland, S. Yao, K. Belfield, S.J. Zheng, S. Barlow, and S. Marder, J. Opt. Soc. Am. B 25, 159 (2008).
&nbsp;<a href="https://doi.org/10.1364/JOSAB.25.000159">https://doi.org/10.1364/JOSAB.25.000159</a>
</li>
<li> Q.D. Zheng, G.S. He, and P.N. Prasad, Chem. Phys. Lett. 475, 250 (2009).
&nbsp;<a href="https://doi.org/10.1016/j.cplett.2009.05.040">https://doi.org/10.1016/j.cplett.2009.05.040</a>
</li>
<li> K.D. Belfield and K.J. Schafer, Chem. Mater. 14, 3656 (2002).
&nbsp;<a href="https://doi.org/10.1021/cm010799t">https://doi.org/10.1021/cm010799t</a>
</li>
<li> C.C. Corredor, Z.L. Huang, K.D. Belfield, A.R. Morales, and M.V. Bondar, Chem. Mater. 19, 5165 (2007).
&nbsp;<a href="https://doi.org/10.1021/cm071336b">https://doi.org/10.1021/cm071336b</a>
</li>
<li> K.J. Schafer, J.M. Hales, M. Balu, K.D. Belfield, E.W. Van Stryland, and D.J. Hagan, J. Photoch. Photobio. A 162, 497 (2004).
&nbsp;<a href="https://doi.org/10.1016/S1010-6030(03)00394-0">https://doi.org/10.1016/S1010-6030(03)00394-0</a>
</li>
<li> K.D. Belfield, M.V. Bondar, F.E. Hernandez, and O.V. Przhonska, J. Phys. Chem. C 112, 5618 (2008).
&nbsp;<a href="https://doi.org/10.1021/jp711950z">https://doi.org/10.1021/jp711950z</a>
</li>
<li> P.L. Wu, X.J. Feng, H.L. Tam, M.S. Wong, and K.W. Cheah, J. Am. Chem. Soc. 131, 886 (2009).
&nbsp;<a href="https://doi.org/10.1021/ja806703v">https://doi.org/10.1021/ja806703v</a>
</li>
<li> M. Velusamy, J.-Y. Shen, J.T. Lin, Y.-C. Lin, C.-C. Hsieh, C.-H. Lai, C.-W. Lai, M.-L. Ho, Y.-C. Chen, P.-T. Chou and J.-K. Hsiao, Adv. Funct. Mater. 19, 2388 (2009).
&nbsp;<a href="https://doi.org/10.1002/adfm.200900125">https://doi.org/10.1002/adfm.200900125</a>
</li>
<li> S.J. Andrasik, K.D. Belfield, M.V. Bondar, F.E. Hernandez, A.R. Morales, O.V. Przhonska, and S. Yao, Chem. Phys. Chem. 8, 399 (2007).
&nbsp;<a href="https://doi.org/10.1002/cphc.200600568">https://doi.org/10.1002/cphc.200600568</a>
</li>
<li> A. Hayek, F. Bolze, J.F. Nicoud, P.L. Baldeck, and Y. Mely, Photochem. Photobio. Sci. 5, 102 (2006).
&nbsp;<a href="https://doi.org/10.1039/B509843B">https://doi.org/10.1039/B509843B</a>
</li>
<li> A.R. Morales, K.J. Schafer-Hales, A.I. Marcus, and K.D. Belfield, Bioconj. Chem. 19, 2559 (2008).
&nbsp;<a href="https://doi.org/10.1021/bc800415t">https://doi.org/10.1021/bc800415t</a>
</li>
<li> K.J. Schafer-Hales, K.D. Belfield, S. Yao, P.K. Frederiksen, J.M. Hales, and P.E. Kolattukudy, J. Biomed. Opt. 10, 051402/1 (2005).
</li>
<li> K. Konig, J. Microsc. 200, 83 (2000).
&nbsp;<a href="https://doi.org/10.1046/j.1365-2818.2000.00738.x">https://doi.org/10.1046/j.1365-2818.2000.00738.x</a>
</li>
<li> R.M. Williams, W.R. Zipfel, and W.W. Webb, Curr. Opin. Chem. Biol. 5, 603 (2001).
&nbsp;<a href="https://doi.org/10.1016/S1367-5931(00)00241-6">https://doi.org/10.1016/S1367-5931(00)00241-6</a>
</li>
<li> D.W. Piston, Trends Cell Biol. 9, 66 (1999).
&nbsp;<a href="https://doi.org/10.1016/S0962-8924(98)01432-9">https://doi.org/10.1016/S0962-8924(98)01432-9</a>
</li>
<li> T.R. Krishna, M. Parent, M.H. Werts, L. Moreaux, S. Gmouh, S. Charpak, A.-M. Caminade, J.-P. Majoral, and M. Blanchard-Desce, Angew. Chem. Int. Ed. 45, 4645 (2006).
&nbsp;<a href="https://doi.org/10.1002/anie.200601246">https://doi.org/10.1002/anie.200601246</a>
</li>
<li> C. Xu and W.W. Webb, J. Opt. Soc. Am. B 13, 481(1996).
&nbsp;<a href="https://doi.org/10.1364/JOSAB.13.000481">https://doi.org/10.1364/JOSAB.13.000481</a>
</li>
<li> P. Kaatz and D.P. Shelton, J. Opt. Soc. Am. B 16, 998 (1999).
&nbsp;<a href="https://doi.org/10.1364/JOSAB.16.000998">https://doi.org/10.1364/JOSAB.16.000998</a>
</li>
<li> W.J. Yang, M.S. Seo, X.Q. Wang, S.J. Jeon, and B.R. Cho, J. Fluoresc. 18, 403 (2008).
&nbsp;<a href="https://doi.org/10.1007/s10895-007-0280-3">https://doi.org/10.1007/s10895-007-0280-3</a>
</li>
<li> K.D. Belfield, M.V. Bondar, O.V. Przhonska, K.J. Schafer, and W. Mourad, J. Lumin. 97, 141 (2002).
&nbsp;<a href="https://doi.org/10.1016/S0022-2313(02)00216-8">https://doi.org/10.1016/S0022-2313(02)00216-8</a>
</li>
<li> K.D. Belfield, M.V. Bondar, O.V. Przhonska, and K.J. Schafer, J. Fluoresc. 12, 449 (2002).
&nbsp;<a href="https://doi.org/10.1023/A:1021322228428">https://doi.org/10.1023/A:1021322228428</a>
</li>
<li> C.C. Corredor, K.D. Belfield, M.V. Bondar, O.V. Przhonska, and S. Yao, J. Photoch. Photobio. A 184, 105 (2006).
&nbsp;<a href="https://doi.org/10.1016/j.jphotochem.2006.03.036">https://doi.org/10.1016/j.jphotochem.2006.03.036</a>
</li>
<li> X. Wang, S. Yao, H.-Y. Ahn, Y. Zhang, M.V. Bondar, J.A. Torres, and K.D. Belfield, Biomed. Opt. Express 1, 453 (2010).
&nbsp;<a href="https://doi.org/10.1364/BOE.1.000453">https://doi.org/10.1364/BOE.1.000453</a>
</li>
<li> X. Wang, D.M. Nguyen, C.O. Yanez, L. Rodriguez, H.-Y. Ahn, M.V. Bondar, and K.D. Belfield, J. Am. Chem. Soc. 132, 12237 (2010).
&nbsp;<a href="https://doi.org/10.1021/ja1057423">https://doi.org/10.1021/ja1057423</a>
</li>
<li> C.D. Andrade, C.O. Yanez, M.A. Qaddoura, X. Wang, C.L. Arnett, S.A. Coombs, R. Bassiouni, M.V. Bondar, and K.D. Belfield, J. Fluoresc. 21, 1223 (2011).
&nbsp;<a href="https://doi.org/10.1007/s10895-010-0801-3">https://doi.org/10.1007/s10895-010-0801-3</a>
</li>
<li> K.D. Belfield, A.R. Morales, B.S. Kang, J.M. Hales, D.J. Hagan, E.W. Van Stryland, V.M. Chapela, and J. Percino, Chem. Mater. 16, 4634 (2004).
&nbsp;<a href="https://doi.org/10.1021/cm049872g">https://doi.org/10.1021/cm049872g</a>
</li>
<li> K.D. Belfield, A.R. Morales, J.M. Hales, D.J. Hagan, E.W. Van Stryland, V.M. Chapela, and J. Percino, Chem. Mater. 16, 2267 (2004).
&nbsp;<a href="https://doi.org/10.1021/cm035253g">https://doi.org/10.1021/cm035253g</a>
</li>
<li> J.P. Moreno and M.G. Kuzyk, J. Chem. Phys. 123, 194101/1 (2005).
</li>
<li> M.G. Kuzyk, J. Chem. Phys. 125, 154108/1 (2006).
</li>
<li> O.S. Finikova, T. Troxler, A. Senes, W.F. DeGrado, R.M. Hochstrasser, and S.A. Vinogradov, J. Phys. Chem. A 111, 6977 (2007).
&nbsp;<a href="https://doi.org/10.1021/jp071586f">https://doi.org/10.1021/jp071586f</a>
</li>
<li> P.A. Padmawar, J.E. Rogers, G.S. He, L.Y. Chiang, L.S. Tan, T. Canteenwala, Q.D. Zheng, J.E. Slagle, D.G. McLean, P.A. Fleitz, and P.N. Prasad, Chem. Mater. 18, 4065 (2006).
&nbsp;<a href="https://doi.org/10.1021/cm060718z">https://doi.org/10.1021/cm060718z</a>
</li>
<li> M. Sheik-Bahae, A.A. Said, T.H. Wei, D.J. Hagan, and E.W. Van Stryland, IEEE J. Quantum Elect. 26, 760 (1990).
&nbsp;<a href="https://doi.org/10.1109/3.53394">https://doi.org/10.1109/3.53394</a>
</li>
<li> M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.J.A. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ц. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox, Gaussian (Wallingford, CT, 2009).
</li>
<li> A. Picot, C. Feuvrie, C. Barsu, F. Malvolti, B. Le Guennic, H. Le Bozec, C. Andraud, L. Toupet, and O. Maury, Tetrahedron 64, 399 (2008).
&nbsp;<a href="https://doi.org/10.1016/j.tet.2007.10.064">https://doi.org/10.1016/j.tet.2007.10.064</a>
</li>
<li> J.R. Lakowicz, Principles of Fluorescence Spectroscopy (Springer, New York, 2006).
&nbsp;<a href="https://doi.org/10.1007/978-0-387-46312-4">https://doi.org/10.1007/978-0-387-46312-4</a>
</li>
<li> G. Luchita, M.V. Bondar, S. Yao, I.A. Mikhailov, C.O. Yanez, O.V. Przhonska, A.E. Masunov, and K.D. Belfield, Appl. Mater. Interf. 3, 3559 (2011).
&nbsp;<a href="https://doi.org/10.1021/am200783c">https://doi.org/10.1021/am200783c</a>
</li>
<li> L.A. Padilha, S. Webster, O.V. Przhonska, H.H. Hu, D. Peceli, J.L. Rosch, M.V. Bondar, A.O. Gerasov, Y.P. Kovtun, M.P. Shandura, A.D. Kachkovski, D.J. Hagan, and E.W. Van Stryland, J. Mater. Chem. 19, 7503 (2009).
&nbsp;<a href="https://doi.org/10.1039/b907344b">https://doi.org/10.1039/b907344b</a>
</li>
<li> J. Fu, L.A. Padilha, D.J. Hagan, E.W. Van Stryland, O.V. Przhonska, M.V. Bondar, Y.L. Slominsky, and A.D. Kachkovski, J. Opt. Soc. Am. B 24, 67 (2007).
&nbsp;<a href="https://doi.org/10.1364/JOSAB.24.000067">https://doi.org/10.1364/JOSAB.24.000067</a>
</li>
<li> B.J. Orr and J.F. Ward, Mol. Phys. 20, 513 (1971).
&nbsp;<a href="https://doi.org/10.1080/00268977100100481">https://doi.org/10.1080/00268977100100481</a>
</li>
<li> K. Ohta, L. Antonov, S. Yamada, and K. Kamada, J. Chem. Phys. 127, (2007).
</li>
<li> A.S. Tatikolov, Z.A. Krasnaya, L.A. Shvedova, and V.A. Kuzmin, Int. J. Photoenergy 2, 23 (2000).
&nbsp;<a href="https://doi.org/10.1155/S1110662X00000040">https://doi.org/10.1155/S1110662X00000040</a>
</li>
<li> J.B. Birks and D.J. Dyson, Proc. R. Soc. Lond. A 275, 135 (1963).
&nbsp;<a href="https://doi.org/10.1098/rspa.1963.0159">https://doi.org/10.1098/rspa.1963.0159</a>
</li>
<li> K.D. Belfield, M.V. Bondar, J.M. Hales, A.R. Morales, O.V. Przhonska, and K.J. Schafer, J. Fluoresc. 15, 3 (2005).
&nbsp;<a href="https://doi.org/10.1007/s10895-005-0207-9">https://doi.org/10.1007/s10895-005-0207-9</a>
</li>
<li> K.D. Belfield, M.V. Bondar, F.E. Hernandez, A.R. Morales, O.V. Przhonska, and K.J. Schafer, Appl. Optics 43, 6339 (2004).
&nbsp;<a href="https://doi.org/10.1364/AO.43.006339">https://doi.org/10.1364/AO.43.006339</a>
</li>
<li> K.D. Belfield, M.V. Bondar, F.E. Hernandezt, O.V. Przhonska, and S. Yao, J. Phys. Chem. B 111, 12723 (2007).
&nbsp;<a href="https://doi.org/10.1021/jp074456f">https://doi.org/10.1021/jp074456f</a>
</li>
<li> K. Kamada, K. Ohta, Y. Iwase, and K. Kondo, Chem. Phys. Lett. 372, 386 (2003).
&nbsp;<a href="https://doi.org/10.1016/S0009-2614(03)00413-5">https://doi.org/10.1016/S0009-2614(03)00413-5</a>
</li>
<li> O.K. Nag, C.S. Lim, B.L. Nguyen, B. Kim, J. Jang, J.H. Han, B.R. Cho, and H.Y. Woo, J. Mater. Chem. 22, 1977 (2012).
&nbsp;<a href="https://doi.org/10.1039/C1JM14693A">https://doi.org/10.1039/C1JM14693A</a>
</li>
<li> V.L. Anderson and W.W. Webb, BMC Biotechnol. 11:125, 1 (2011).
</li>

</ol>
UJP 2013 V58 #8

Downloads

Published

2018-10-10

How to Cite

Bondar, M. V., Przhonska, O. V., Kachkovsky, O. D., Frazer, A., Morales, A. R., & Belfield, K. D. (2018). New Fluorene-Based Fluorescent Probe with Efficient Two-Photon Absorption. Ukrainian Journal of Physics, 58(8), 748. https://doi.org/10.15407/ujpe58.08.0748

Issue

Vol. 58 No. 8 (2013)

Section

Solid matter

License

Copyright Agreement
License to Publish the Paper
Kyiv, Ukraine

The corresponding author and the co-authors (hereon referred to as the Author(s)) of the paper being submitted to the Ukrainian Journal of Physics (hereon referred to as the Paper) from one side and the Bogolyubov Institute for Theoretical Physics, National Academy of Sciences of Ukraine, represented by its Director (hereon referred to as the Publisher) from the other side have come to the following Agreement:

1. Subject of the Agreement.
The Author(s) grant(s) the Publisher the free non-exclusive right to use the Paper (of scientific, technical, or any other content) according to the terms and conditions defined by this Agreement.

2. The ways of using the Paper.
2.1. The Author(s) grant(s) the Publisher the right to use the Paper as follows.
2.1.1. To publish the Paper in the Ukrainian Journal of Physics (hereon referred to as the Journal) in original language and translated into English (the copy of the Paper approved by the Author(s) and the Publisher and accepted for publication is a constitutive part of this License Agreement).
2.1.2. To edit, adapt, and correct the Paper by approval of the Author(s).
2.1.3. To translate the Paper in the case when the Paper is written in a language different from that adopted in the Journal.
2.2. If the Author(s) has(ve) an intent to use the Paper in any other way, e.g., to publish the translated version of the Paper (except for the case defined by Section 2.1.3 of this Agreement), to post the full Paper or any its part on the web, to publish the Paper in any other editions, to include the Paper or any its part in other collections, anthologies, encyclopaedias, etc., the Author(s) should get a written permission from the Publisher.

3. License territory.
The Author(s) grant(s) the Publisher the right to use the Paper as regulated by sections 2.1.1–2.1.3 of this Agreement on the territory of Ukraine and to distribute the Paper as indispensable part of the Journal on the territory of Ukraine and other countries by means of subscription, sales, and free transfer to a third party.

4. Duration.
4.1. This Agreement is valid starting from the date of signature and acts for the entire period of the existence of the Journal.

5. Loyalty.
5.1. The Author(s) warrant(s) the Publisher that:
– he/she is the true author (co-author) of the Paper;
– copyright on the Paper was not transferred to any other party;
– the Paper has never been published before and will not be published in any other media before it is published by the Publisher (see also section 2.2);
– the Author(s) do(es) not violate any intellectual property right of other parties. If the Paper includes some materials of other parties, except for citations whose length is regulated by the scientific, informational, or critical character of the Paper, the use of such materials is in compliance with the regulations of the international law and the law of Ukraine.

6. Requisites and signatures of the Parties.
Publisher: Bogolyubov Institute for Theoretical Physics, National Academy of Sciences of Ukraine.
Address: Ukraine, Kyiv, Metrolohichna Str. 14-b.
Author: Electronic signature on behalf and with endorsement of all co-authors.

Crossref
Scopus
Google Scholar
Europe PMC

Most read articles by the same author(s)