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A theoretical and experimental study of non-linear absorption properties of substituted 2,5-di-(phenylethynyl)thiophenes and structurally related compounds
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2009 (English)In: Molecular Physics, ISSN 0026-8976, E-ISSN 1362-3028, Vol. 107, no 7, 629-641 p.Article in journal (Refereed) Published
Abstract [en]

Photo-physical properties relevant for optical power limiting in the near-visible and visible regions of the spectrum are reported for a series of substituted diarylalkynyl chalcogenophenes (furans, thiophenes, selenophenes, and tellurophenes). The linear ground and excited state absorption as well as the nonlinear (two-photon) absorption were determined at the time-dependent density functional theory level with use of the hybrid exchange-correlation functionals B3LYP and CAM-B3LYP. A selected number of the theoretically studied molecules were synthesized and characterized experimentally with the use of absorption and luminescence spectroscopy. The photo-physical data are compared to the results from optical power limiting measurements performed in THF solution at a wavelength of 532 nm, with a laser pulse length of 5 ns and pulse energies up to 150 J. The best compounds in the present investigation display an energy damping by approximately a factor of 10 at a concentration of 0.010 M.

Place, publisher, year, edition, pages
2009. Vol. 107, no 7, 629-641 p.
Keyword [en]
Chalcogenophenes, Density functional theory, DFT, Excited state absorption, Optical limiting, Thiophenes, TPA, Two-photon absorption, Absorption, Absorption spectroscopy, Excited states, Light absorption, Luminescence of organic solids, Multiphoton processes, Optical materials, Optical properties, Organic polymers, Photons, Power spectrum, Probability density function, Pulsed laser applications, Thiophene
National Category
Theoretical Chemistry
URN: urn:nbn:se:kth:diva-198760DOI: 10.1080/00268970902845289ISI: 000266199000003ScopusID: 2-s2.0-67651250965OAI: diva2:1059051

References: Prasad, P.N., Reinhardt, B.A., (1990) Chem. Mater, 2, p. 660; Bredas, J.L., Adant, C., Tackx, P., Persoons, A., Pierce, B.M., (1994) Chem. Rev, 94, p. 243; Stegeman, G.I., (1997) Nonlinear Optical Organic Molecular Polymers, p. 799. , edited by H.S. Nalwa and S. Miyata CRC Press, Boca Raton; Hollins, R.C., (1999) Curr. Opi. Solid State Mater. Sci, 4, p. 189; Kaino, T., (2000) J. Opt. A, Pure Appl. Opt, 2, pp. R1; Zhou, G.J., Wong, W.Y., Ye, C., Lin, Z.Y., (2007) Adv. Funct. Mater, 17, p. 963; He, G.S., Tan, L.-S., Zheng, Q., Prasad, P.N., (2008) Chem. Rev, 108, p. 1245; Ramos-Ortiz, G., Cha, M., Thayumanavan, S., Mendez, J., Marder, S.R., Kippelen, B., (2004) Appl. Phys. Lett, 85, p. 3348; Lee, K.S., Yang, D.Y., Park, S.H., Kim, R.H., (2006) Polym. Adv. Technol, 17, p. 72; Perry, J.W., (1997) Nonlinear Optical Organic Molecular Polymers, p. 813. , edited by H.S. Nalwa and S. Miyata CRC Press, Boca Raton; Spangler, C.W., (1999) J. Mater. Chem, 9, p. 2013; Dini, D., Barthel, M., Hanack, M., (2001) Eur. J. Org. Chem, 2001, p. 3759; Ehrlich, J.E., Wu, X.L., Lee, I.Y.S., Hu, Z.Y., Rockel, H., Marder, S.R., Perry, J.W., (1997) Opt. Lett, 22, p. 1843; Reinhardt, B.A., Brott, L.L., Clarson, S.J., Dillard, A.G., Bhatt, J.C., Kannan, R., Yuan, L.X., Prasad, P.N., (1998) Chem. Mater, 10, p. 1863; Rogers, J.E., Hall, B.C., Hufnagle, D.C., Slagle, J.E., Ault, A.P., McLean, D.G., Fleitz, P.A., Cooper, T.M., (2005) J. Chem. Phys, 122, p. 214708; Nalwa, H.S., (1997) Nonlinear Optical Organic Molecular Polymers, p. 611. , edited by H.S. Nalwa and S. Miyata CRC Press, Boca Raton; Badaeva, E., Tretiak, S., (2008) Chem. Phys. Lett, 450, p. 322; Xing, X.J., Li, J., Sun, Y.P., Wang, C.K., (2008) Theochem-J. Mol. Struct, 849, p. 116; Ogawa, K., Kobuke, Y., (2006) J. Photochem. Photobiol. C, 7, p. 1; Lind, P., Lopes, C., Öberg, K., Eliasson, B., (2004) Chem. Phys. Lett, 387, p. 238; Lind, P., Eriksson, A., Lopes, C., Eliasson, B., (2005) J. Phys. Org. Chem, 18, p. 426; Vestberg, R., Nilsson, C., Lopes, C., Lind, P., Eliasson, B., Malmström, E., (2005) J. Polym. Sci., Part A: Polym. Chem, 43, p. 1177; Staromlynska, J., McKay, T.J., Wilson, P., (2000) J. Appl. Phys, 88, p. 1726; Vestberg, R., Westlund, R., Eriksson, A., Lopes, C., Carlsson, M., Eliasson, B., Glimsdal, E., Malmstrom, E., (2006) Macromolecules, 39, p. 2238; M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, 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, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. WoBecke, A.D., (1993) J. Chem. Phys, 98, p. 5648; Dunning, T.H., (1989) J. Chem. Phys, 90, p. 1007; Bergner, A., Dolg, M., Kuchle, W., Stoll, H., Preuss, H., (1993) Mol. Phys, 80, p. 1431;, DALTON, a molecular electronic structure program, Release 2.0 2005, seeYanai, T., Tew, D.P., Handy, N.C., (2004) Chem. Phys. Lett, 393, p. 51; Peach, M.J.G., Helgaker, T., Salek, P., Keal, T.W., Lutnaes, O.B., Tozer, D.J., Handy, N.C., (2006) Phys. Chem. Chem. Phys, 8, p. 558; Hehre, W.J., Ditchfield, R., Pople, J.A., (1972) J. Chem. Phys, 56, p. 2257; Norman, P., Ruud, K., (2006) Nonlinear Optical Properties of Matter: From Molecules to Condensed Phases, pp. 1-49. , edited by M.G. Papadopoulos, A.J. Sadlej, and J. Leszczynski Springer, Dordrecht; Samoc, M., Dalton, G.T., Gladysz, J.A., Zheng, Q., Velkov, Y., Agren, H., Norman, P., Humphrey, M.G., (2008) Inorg. Chem, 47, p. 9946; Vincent, D., Cruickshank, J., (1997) Appl. Opt, 36, p. 7794; D. Vincent, MCLC S&T, Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. B: Nonlinear Optics 21, 413 (1999)Demas, J.N., Crosby, G.A., (1971) J. Phys. Chem, 75, p. 991; Williams, A.T.R., Winfield, S.A., Miller, J.N., (1983) Analyst, 108, p. 1067; Sonogashira, K., Tohda, Y., Hagihara, N., (1975) Tetrahedron Lett, 16, p. 4467; Keegstra, M.A., Klomp, A.J.A., Brandsma, L., (1990) Synth. Commun, 20, p. 3371; Jung, T.S., Kim, J.H., Jang, E.K., Kim, D.H., Shim, Y.-B., Park, B., Shin, S.C., (2000) J. Organomet. Chem, 599, p. 232; Gronowitz, S., Frejd, T., (1976) Acta Chem. Scand., Ser. B, B30, p. 313; Greaves, S.J., Flynn, E.L., Futcher, E.L., Wrede, E., Lydon, D.P., Low, P.J., Rutter, S.R., Beeby, A., (2006) J. Phys. Chem. A, 110, p. 2114; Siddle, J.S., Ward, R.M., Collings, J.C., Rutter, S.R., Porres, L., Applegarth, L., Beeby, A., Marder, T.B., (2007) New J. Chem, 31, p. 841; Norman, P., Cronstrand, P., Ericsson, J., (2002) Chem. Phys, 285, p. 207; Henriksson, J., Norman, P., Jensen, H.J.A., (2005) J. Chem. Phys, 122, p. 114106; Henriksson, J., Ekstrom, U., Norman, P., (2006) J. Chem. Phys, 124, p. 214311; D. Jacquemin, E.A. Perpete, G.E. Scuseria, I. Ciofini, and C. Adamo, J. Chem. Theory Comput. 4, 123 (2008)Peach, M.J.G., Benfield, P., Helgaker, T., Tozer, D.J., (2008) J. Chem. Phys, 128, p. 044118; Paterson, M.J., Christiansen, O., Pawlowski, F., Jorgensen, P., Hattig, C., Helgaker, T., Salek, P., (2006) J. Chem. Phys, 124, p. 054322; Yasuda, T., Imase, T., Nakamura, Y., Yamamoto, T., (2005) Macromolecules, 38, p. 4687; Baev, A., Norman, P., Henriksson, J., Agren, H., (2006) J. Phys. Chem. B, 110, p. 20912; Baev, A., Welinder, P., Erlandsson, R., Henriksson, J., Norman, P., Agren, H., (2007) J. Nonlinear Opt. Phys. Mater, 16, p. 157; Dobrin, S., Kaszynski, P., Waluk, J., (1997) J. Photochem. Photobiol A, 105, p. 149; Ohulchanskyy, T.Y., Donnelly, D.J., Detty, M.R., Prasad, P.N., (2004) J. Phys. Chem. B, 108, p. 8668; Chattopadhyay, S.K., Craig, B.B., (1987) J. Phys. Chem, 91, p. 323; Hurley, R., Testa, A.C., (1968) J. Am. Chem. Soc, 90, p. 1949; Lorenc, J., Kucharska, E., Hanuza, J., Chojnacki, H., (2004) J. Mol. Struct, 707, p. 47. QC 20170117

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