Jump to ContentJump to Main Navigation
Show Summary Details
In This Section

Organic Photonics and Photovoltaics

Editor-in-Chief: Facchetti, Antonio

Ed. by Ponomarenko, Sergei

1 Issue per year


Emerging Science

Open Access
Online
ISSN
2299-3177
See all formats and pricing
In This Section

Spectral properties and photophysics of arylacetylenes in thin films

Rebecca Flamini
  • Department of Chemistry, and Centro di Eccellenza sui Materiali Innovativi Nanostrutturati (CEMIN), University of Perugia, via Elce di Sotto 8, 06123 Perugia, Italy
/ Benedetta Carlotti
  • Department of Chemistry, and Centro di Eccellenza sui Materiali Innovativi Nanostrutturati (CEMIN), University of Perugia, via Elce di Sotto 8, 06123 Perugia, Italy
/ Anna Spalletti
  • Department of Chemistry, and Centro di Eccellenza sui Materiali Innovativi Nanostrutturati (CEMIN), University of Perugia, via Elce di Sotto 8, 06123 Perugia, Italy
/ Assunta Marrocchi
  • Department of Chemistry, and Centro di Eccellenza sui Materiali Innovativi Nanostrutturati (CEMIN), University of Perugia, via Elce di Sotto 8, 06123 Perugia, Italy
Published Online: 2014-02-19 | DOI: https://doi.org/10.2478/oph-2014-0001

Abstract

We report the photobehaviour of a series of eight structurally related arylacetylene derivatives, in solution as well as in pristine and PC61BM blended thin-_lms. The formation of both H- and J-aggregates in the solid state have been demonstrated, and, interestingly, an energy transfer from H-aggregates or/and from residual "unstacked" molecules to J-aggregates has been found, the latter being the only emitting species. The fuorescence quenching by PC61BM at di_erent loadings has been studied in blend films, and it has been found particularly effcient in the case of a symmetrical peripheral substitution of the acetylene derivative core. Preliminary time-resolved measurements in emission (ns resolution) and in absorption (fs resolution) con_rmed the H⟶J energy transfer and underlined the presence of delayed fuorescence from Jaggregates, formed by energy transfer from the long-lived first excited singlet state of H-aggregates. In all cases, a homogeneous surface morphology of thin films.

Keywords: small molecule organic semiconductors; thin film; J-aggregate; H-aggregate; energy transfer

PACS: 78.20.-e; 78.40.Fy; 78.47.jb; 78.66.Sq; 78.66.Qn

References

  • [1] H. Xin, X. Guo, G.. Ren, M.D. Watson, S. A. Jenekhe, Adv. En. Mater. 2, 575(2012)

  • [2] A. Marrocchi, D. Lanari, A. Facchetti, A., L. Vaccaro, En. Eviron. Sci. 5, 8457 (2012)

  • [3] P.-Y. Huang, L.-H. Chen, C. Kim, C. Hsiu-Chieh, Y.-J. Liang, C.- Y. Feng, C.-M. Yeh, J.-C. Ho, C.-C. Lee, M.-C. Chen, ACS Appl. Mater. Interfaces 4, 6992 (2012)

  • [4] T. S. van der Poll, J. A. Love, T.-Q. Nguyen, G. C. Bazan, Adv. Mater. 24, 3646 (2012)

  • [5] A. Facchetti, Chem. Mater. 23, 733 (2011)

  • [6] A. Facchetti, L. Vaccaro, A. Marrocchi, Angew. Chem. Int. Ed. 51, 3520 (2012)

  • [7] P. Berrouard, A. Najari, A. Pron, D. Gendron, P.-O. Morin, J.-R. Pouliot, J. Veilleux, M. Leclerc, Angew. Chem. Int. Ed. 51, 2068 (2012)

  • [8] A. Marrocchi, Curr. Org. Synth. 9, 149 (2012)

  • [9] M. Hasegawa, M. Iyoda, Chem. Soc. Rev. 39, 2429 (2010)

  • [10] M. Leclerc, J.-F. Morin (eds.), Design and Synthesis of Conjugated Polymers (Wiley-VCH, Weinheim, 2010)

  • [11] A.C. Grimsdale, K. L. Chan, R. E. Martin, P. G. Jokisz, A. B. Holmes, Chem. Rev. 109, 897 (2009).

  • [12] A. Heeger, F. Hide, B. Schwartz, M. A. Diaz-Garcia, Chem Phys. Lett. 256, 424 (1996).

  • [13] C. Li, Y. Li, Macromol. Chem. Phys. 209, 1541 (2008)

  • [14] F. Diederich, P. J. Stang, R. R. Tykwinski (eds), Acetylene Chemistry: Chemistry, Biology, and Materials Science (Wiley-VCH: Weinheim, Germany, 2005)

  • [15] Bunz, U. H.F. Chem. Rev. 100, 1605 (2000). [PubMed]

  • [16] W. Zhang, S.M. Kraft, J. S. Moore, J. Am. Chem. Soc. 126, 329 (2004)

  • [17] P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. Int. Ed. 39, 2632 (2000)

  • [18] K. Sonogashira, Metal Catalyzed cross-coupling reactions (Wiley-VCH, Weinheim, Germany, 1998)

  • [19] K. Weiss, A. Michel, E.-M. Auth, E.H.F. Bunz, T. Mangel, K. Mullen, Angew. Chem. Int. Ed. 25, 506 (1997)

  • [20] R.R. Schrock, Polyhedron 14, 3177 (1995).

  • [21] W. A, Braunecker, S. D. Oosterhout, Z. R. Owczarczyk, R. E. Larsen, B. W. Larson, D. S. Ginley, O. V. Boltalina, S. H. Strauss, N. Kopidakis, D. C. Olson, Macromolecules 46, 3367 (2013)

  • [22] C. Kästner, S. Rathgeber, D.A.M. Egbe, H. Hoppe, J. Mater. Chem. A 1, 3961 (2013)

  • [23] S. Rochat, T. M. Swager, ACS Appl. Mater. Interface 5, 4488 (2013)

  • [24] C. Kästner, B. Muhsin, A. Wild, D. A. M Egbe, S. Rathgeber, H. Hoppe, J. Polym. Sci. B 51, 868 (2013)

  • [25] A. Operamolla, R. Ragni, O. H. Omar, G. Iacobellis, A. Cardone, F. Babudri, G. Farinola, Curr. Org. Synth. 9, 764 (2012)

  • [26] A. Marrocchi, I. Tomasi, L. Vaccaro, Isr. J. Org. Chem. 52, 42 (2012)

  • [27] F. Silvestri, A. Marrocchi, Int. J. Mol. Sci. 11, 1471 (2010)

  • [28] A.C Grimsdale, K. L. Chan, R.E Martin, P.G Jokisz, A.B Holmes, Chem. Soc. Rev. 109, 897 (2009).

  • [29] Q. Niu, Y. Lu, H. Sun, X. Li, X. Tao, Dyes and Pigments 97, 184 (2013)

  • [30] F. Feng, J. Yang, D. Xie, T. D. McCarley, K. S. Schanze, J. Phys. Chem. Lett. 4, 1410 (2013)

  • [31] B. A. Coombs, S. R. Rutter, A. E. Goeta, H. A. Sparkes, A. S. Batsanov, A. Beeby, RSC Adv. 2, 1870 (2012)

  • [32] S. Cook, H. Ohkita, Y. Kim, J. J. Benson-Smith, D. D. C. Bradley, J. R. Durrant, Chem. Phys. Lett. 445, 276 (2007)

  • [33] K.-Y. Pu, B. Zhang, Z. Ma, P. Wang, X.-Y. Qi, R.-F. Chen, L.-H. Wang, Q.-L. Fan, W. Huang, Polymer 47, 1970 (2006)

  • [34] P. V. James, P. K. Sudeep, C. H. Suresh, K. G. Thomas, J. Phys. Chem. A 110, 4329 (2006)

  • [35] U. H. F. Bunz, J. M. Imhof, R. K. Bly, C. G. Bangcuyo, L. Rozanski, D. A. Vanden Bout, Macromolecules 38, 5892 (2005)

  • [36] M. Levitus, G. Zepeda, H. Dang, C. Godinez, T.-A. V. Khuong, K. Schmieder, M. A. Garcia-Garibay, J. Org. Chem. 66, 3188 (2001).

  • [37] E. Bartollini, M. Seri, S. Tortorella, A. Facchetti, T. J. Marks, A. Marrocchi, L. Vaccaro, RSC Adv. 3, 9288 (2013)

  • [38] M. Seri, A. Marrocchi, D. Bagnis, R. Ponce, A. Taticchi, T.J. Marks, A. Facchetti, Adv. Mater. 23, 3827 (2011)

  • [39] P. Wolfer, M. L. Santarelli, L. Vaccaro, L. Yu, T. D. Anthopulos, P. Smith, N. Stingelin, A. Marrocchi, Org. Electron. 12, 1886 (2011)

  • [40] F. Silvestri, A. Marrocchi, M. Seri, C. Kim, A. Facchetti, A. Taticchi, T. J. Marks, J. Am. Chem. Soc. 132, 6109 (2010)

  • [41] A. Marrocchi, F. Silvestri, M. Seri, A. Facchetti, A. Taticchi, T. J. Marks. Chem. Commun., 1380 (2009)

  • [42] A. Marrocchi, M. Seri, C. Kim, A. Facchetti, A. Taticchi, T. J. Marks, Chem. Mater. 21, 2592 (2009)

  • [43] S. R. Saudari, Y. J. Lin, Y. Lai, C. R. Kagan, Adv. Mater. 22, 5063 (2010)

  • [44] H. Yan, Y. Zheng, R. Blache, C. Newman, S. Lu, J. Woerle, A. Facchetti, Adv. Mater. 20, 3393 (2008).

  • [45] A. K. K. Kyaw, D. H. Wang, D. Wynands, J. Zhang, T.-Q. Nguyen, G. C. Bazan, A. J. Heeger, Nano Lett. 13, 3796 (2013). [PubMed]

  • [46] R. Flamini, I. Tomasi, A. Marrocchi, B. Carlotti, A. Spalletti, J. Photochem. Photobiol. A 223, 140 (2011)

  • [47] A. Marrocchi, A. Spalletti, S. Ciorba, M. Seri, F. Elisei, A. Taticchi, J. Photochem. Photobiol. A 211, 162 (2010)

  • [48] I. Votta, A. Marrocchi, L. Vaccaro, unpublished results.

  • [49] B. Carlotti, D. Fuoco, F. Elisei, Phys. Chem. Chem. Phys. 12, 15580, (2010).

  • [50] T. Del Giacco, B. Carlotti, A. Barbafina, S. De Solis and F. Elisei, Phys. Chem. Chem. Phys. 13, 2188 (2011). [Crossref]

  • [51] A. Mishra, R. K. Behera, P. K. Behera, B. K. Mishra, G. B. Behera, Chem. Rev. 100, 1973 (2000) and references therein.

  • [52] M. Kasha, H.R. Rawls, M.A. El-Bayoumi, Pure Appl. Chem. 11, 371 (1965).

  • [53] S.D. Spencer, C. Bougher, P.J. Heaphy, V.M. Murcia, C.P. Gallivan, A. Monfette, J.D. Andersen, J.A. Cody, Solar Energy Materials & Solar Cells 112, 202 (2013).

  • [54] G. de Miguel, M. Ziólek, M. Zitnan, J.A. Organero, S.S. Pandey, S. Hayase, A. Douhal, J. Phys. Chem. C 116, 9379 (2012).

  • [55] J.-H. Hsu, W. Fann, P.-H. Tsao, K.-R. Chuang, S.-A. Chen, J. Phys. Chem. A 103, 2375 (1999).

  • [56] N.C. Maiti, S. Mazumdar, N. Periasamy, J. Phys. Chem. B 102, 1528 (1998).

About the article


Received: 2013-10-21

Accepted: 2013-10-26

Published Online: 2014-02-19



Citation Information: Organic Photonics and Photovoltaics, ISSN (Online) 2299-3177, DOI: https://doi.org/10.2478/oph-2014-0001. Export Citation

©2014 Anna Spalletti et al.. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. (CC BY-NC-ND 3.0)

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
G. Cacioppa, B. Carlotti, F. Elisei, P. L. Gentili, A. Marrocchi, and A. Spalletti
Phys. Chem. Chem. Phys., 2016, Volume 18, Number 1, Page 285
[2]
[3]
Rebecca Flamini, Assunta Marrocchi, and Anna Spalletti
Photochemical & Photobiological Sciences, 2014, Volume 13, Number 7, Page 1031

Comments (0)

Please log in or register to comment.
Log in