Hostname: page-component-78c5997874-m6dg7 Total loading time: 0 Render date: 2024-11-19T17:58:59.531Z Has data issue: false hasContentIssue false

Electrosynthesis of thin films of polythiophenes containing pyrene groups and flexible spacers, useful in the preparation of graphene polymer composites

Published online by Cambridge University Press:  04 November 2019

Bianca X. Valderrama-García
Affiliation:
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior Ciudad Universitaria C.P.04510, Ciudad de México, México. CNRS; LCC (Laboratoire de Chimie de Coordination); 205, route de Narbonne, 31077Toulouse, France
Israel González-Méndez
Affiliation:
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior Ciudad Universitaria C.P.04510, Ciudad de México, México.
Alix Sournia-Saquet
Affiliation:
CNRS; LCC (Laboratoire de Chimie de Coordination); 205, route de Narbonne, 31077Toulouse, France Université de Toulouse; UPS, INP; LCC; 31077Toulouse, France
Marine Tasse
Affiliation:
CNRS; LCC (Laboratoire de Chimie de Coordination); 205, route de Narbonne, 31077Toulouse, France Université de Toulouse; UPS, INP; LCC; 31077Toulouse, France
Kathleen I. Moineau-Chane Ching*
Affiliation:
CNRS; LCC (Laboratoire de Chimie de Coordination); 205, route de Narbonne, 31077Toulouse, France Université de Toulouse; UPS, INP; LCC; 31077Toulouse, France
Ernesto Rivera*
Affiliation:
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior Ciudad Universitaria C.P.04510, Ciudad de México, México.
*
*kathleen.chane@lcc-toulouse.fr (K. M. C.); Tel.: +33 561 33 31 33 riverage@unam.mx (E.R.), Tel.: +52 55 56 22 47 33
*kathleen.chane@lcc-toulouse.fr (K. M. C.); Tel.: +33 561 33 31 33 riverage@unam.mx (E.R.), Tel.: +52 55 56 22 47 33
Get access

Abstract

Thin polythiophene films were prepared by electrodeposition, using two novel thiophene monomers containing a pyrene unit linked via a flexible spacer. The obtained polymers have a suitable architecture for the further preparation of polymer composites with graphene via π-π interactions. Physicochemical characterization of the precursor polymers demonstrated that the resulting films are made of homogeneous electroactive polythiophene with pendant pyrene units regularly located on the polymer surface. These compounds are highly emissive and easily form excimers as other high pyrene content polymers. The polymer emission can be drastically quenched by the interaction with graphene after dipping the film into an aqueous suspension of reduced graphite oxide. The presence of aggregated graphene onto pyrene rich content areas by non-covalent interactions has been confirmed by AFM analysis. This kind of polythiophene/pyrene thin films showed to be a good matrix for the elaboration of fluorescent polymer composites.

Type
Articles
Copyright
Copyright © Materials Research Society 2019 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Geim, A.K., Novoselov, K.S., Nat. Mater. 6 (2007) 183191.CrossRefGoogle Scholar
Novoselov, K.S., K Geim, A., Morozov, S.V., Jiang, D., Zhang, Y., Dubonos, S.V., Grigorieva, I.V., Firsov, A.A., Science 306 (2004) 666669.CrossRefGoogle Scholar
Xu, Y., Wang, Y., Liang, J., Huang, Y., Ma, Y., Wan, X., Chen, Y., Nano Res . 2 (2009) 343348.CrossRefGoogle Scholar
Yang, Z., Shi, X., Yuan, J., Pu, H., Liu, Y., Appl. Surf. Sci. 257 (2010) 138142.CrossRefGoogle Scholar
Wang, X., Wang, J., Cheng, H., Yu, P., Ye, J., Mao, L., Langmuir 27 (2011) 1118011186.CrossRefGoogle Scholar
Li, F., Song, J., Yang, H., Gan, S., Zhang, Q., Han, D., Ivaska, A., Niu, L., Nanotechnology 20 (2009) 455602.CrossRefGoogle Scholar
Tu, W., Lei, J., Zhang, S., Ju, H., Chem. Eur. J. 16 (2010) 1077110777.CrossRefGoogle Scholar
Zeng, G., Xing, Y., Gao, J., Wang, Z., Zhang, X., Langmuir 26 (2010) 1502215026.CrossRefGoogle Scholar
Hong, W., Bai, H., Xu, Y., Yao, Z., Gu, Z., Shi, G., J. Phys. Chem. C 114 (2010) 1822-1826.CrossRefGoogle Scholar
Dikin, D.A., Stankovich, S., Zimney, E.J., Piner, R.D., Dommett, G.H.B., Evmenenko, G., Nguyen, S.T., Ruoff, R.S., Nature 448 (2007) 457460.CrossRefGoogle Scholar
Berger, C., Song, Z., Li, X., Wu, X., Brown, N., Naud, C., Mayou, D., Li, T., Hass, J., Marchenkov, A.N., Conrad, E.H., First, P.N., de Heer, W.A., Science 312 (2006) 11911196.CrossRefGoogle Scholar
Wei, D., Liu, Y., Wang, Y., Zhang, H., Huang, L., Yu, G., Nano Lett . 9 (2009) 17521758.CrossRefGoogle Scholar
Chen, H., Muller, M.B., Gilmore, K.J., Wallace, G.G., Li, D., Adv. Mater. 20 (2008) 3557-3561.CrossRefGoogle Scholar
Li, X.L., Wang, X.R., Zhang, L., W Lee, S., J Dai, H., Science 319 (2008) 12291232.CrossRefGoogle Scholar
Li, X., Zhang, G., Bai, X., Sun, X., Wang, X., Wang, E., Dai, H., Nat. Nanotechnol. 3 (2008) 538542.CrossRefGoogle Scholar
Choucair, M., Thordarson, P., Stride, J.A., Nat. Nanotechnol. 4 (2009) 3033.CrossRefGoogle Scholar
Das, B., Voggu, R., Rout, C.S., Rao, C.N.R., Chem. Commun., 41 (2008), 5155-5157.CrossRefGoogle Scholar
Voggu, R., Das, B., Rout, C.S., Rao, C.N.R., J. Phys.: Condens. Matter 20 (2008) 472204 (1-5).Google Scholar
Subrahmanyam, K.S., Voggu, R., Govindaraj, A., Rao, C.N.R., Chem. Phys. Lett. 472 (2009) 96-98.CrossRefGoogle Scholar
Subrahmanyam, K.S., Ghosh, A., Gomathi, A., Govindaraj, A., Rao, C.N.R., Nanosci. Nanotechnol. Lett. 1 (2009) 28-31.CrossRefGoogle Scholar
Ghosh, A., Rao, K.V., George, S.J., Rao, C.N.R., Chem. Eur.J. 16 (2010) 2700-2704.CrossRefGoogle Scholar
Stepanian, S., Karachevtsev, V.A., Glamazda, A.Y., Dettlaff-Weglikowska, U., L. Mol. Phys. 101 (2003) 2609-2614.CrossRefGoogle Scholar
Xie, Y.H., K Soh, A., Mater. Lett. 59 (2005) 971975.CrossRefGoogle Scholar
Elemans, J.A.A.W., Van Hameren, R., Nolte, R.J.M., E Rowan, A., Adv. Mater. 18 (2006) 1251-1266.CrossRefGoogle Scholar
Guldi, D.M., Rahman, G.M.A., Zerbetto, F., Prato, M., Acc. Chem. Res. 38 (2005) 871878.CrossRefGoogle Scholar
Murakami, H., Nomura, T., Nakashima, N., Chem. Phys. Lett. 378 (2003) 481485.CrossRefGoogle Scholar
Alvaro, M., Aprile, C., Ferrer, B., Garcia, H., J. Am. Chem. Soc. 129 (2007) 56475655.CrossRefGoogle Scholar
Guldi, D.M., Rahman, A., Sgobba, V., Ehli, C., Chem. Soc. Rev. 35 (2006) 471487.CrossRefGoogle Scholar
Martin, R., Alvaro, M., Garcia, H., Curr. Org. Chem. 15 (2011) 11061120.CrossRefGoogle Scholar
Robel, I., Bunker, B.A., Kamat, P.V., Adv. Mater. 17 (2005) 24582463.CrossRefGoogle Scholar
De Miguel, M., Álvaro, M., García, H., Langmuir 28 (2012) 2849-2857.CrossRefGoogle Scholar
Xu, Y., Liu, Z., Zhang, X., Wang, Y., Tian, J., Huang, Y., Ma, Y., Zhang, X., Chen, Y., Adv. Mater. 21 (2009) 1275-1279.CrossRefGoogle Scholar
Xu, Y., Zhao, L., Hong, W., Li, C., Shi, G., J. Am. Chem. Soc. 131 (2009) 13490-13497.CrossRefGoogle Scholar
Swathi, R.S., Sebastian, K.L., J. Chem. Phys 129 (2008) 054703.CrossRefGoogle Scholar
Swathi, R.S., Sebastian, K.L., J. Chem. Phys 130 (2009) 086101.CrossRefGoogle Scholar
Lu, C.H., Yang, H.H., Zhu, C.L., Chen, X., Chen, G.N., Angew. Chem. Int. Ed. 48 (2009) 4785-4787.CrossRefGoogle Scholar
Treossi, E., Melucci, M., Liscio, A., Gazzano, M., Samori, P., Palermo, V., J. Am. Chem. Soc. 131 (2009) 15576-15577.CrossRefGoogle Scholar
Kamat, P.V., J. Phys. Chem. Lett. 1 (2010) 520-527.CrossRefGoogle Scholar
Xie, L., Ling, X., Fang, Y., Zhang, J., Liu, Z., J. Am. Chem. Soc. 131 (2009) 9980- 9981.Google Scholar
Liu, Y., Liu, C.Y., Appl. Surf. Sci. 257 (2010) 55135518.CrossRefGoogle Scholar
Matte, H.,Subrahmanyam, K.S.,Rao, K.V.,George, S.J.,Rao, C.N.R., Chem. Phys. Lett. 506 (2011) 260264.CrossRefGoogle Scholar
Rao, C.N.R., Subrahmanyam, K.S., Matte, H., Govindaraj, A., Mod. Phys. Lett. B 25 (2010) 427451.CrossRefGoogle Scholar
Tian, J.Q., Li, H.L., Luo, Y.L., Wang, L., Zhang, Y.W., , Y. W., Sun, X.P ., Langmuir 27 (2010) 874877.CrossRefGoogle Scholar
Wang, Y.B., Kurunthu, D., Scott, G.W., Bardeen, C.J., J. Phys. Chem. C 114 (2010) 4153-4159.CrossRefGoogle Scholar
Wu, X.M., Cao, H.Q., Li, B.J., Yin, G., Nanotechnology 22 (2011) 75202.CrossRefGoogle Scholar
Zhang, X.F., Xi, Q., Carbon 49 (2011) 38423850.CrossRefGoogle Scholar
Winnik, F.M., Chem. Rev. 93 (1993) 587614.CrossRefGoogle Scholar
Rivera, E., Belletête, M., Zhu, X.X., Durocher, G., Giasson, R., Polymer 43 (2002) 5059-5068.CrossRefGoogle Scholar
Rivera, E., Wang, R., Zhu, X.X., Zargarian, D., Giasson, R., J. Mol. Catal. 204 (2003) 325332.CrossRefGoogle Scholar
Belletête, M., Rivera, E., Giasson, R., Zhu, X.X., Durocher, G., Synth. Met. 14 (2004) 3742.CrossRefGoogle Scholar
Morales-Saavedra, O., Rivera, E., Polymer 47 (2006) 53305337.CrossRefGoogle Scholar
Yoshino, K., Nakajima, S., Onada, M., Sugimoto, R., Synth. Met. 28 (1989) 349357.CrossRefGoogle Scholar
Valderrama-García, B.X., I Moineau-Chane Ching, K., Rivera, E., Molecules 21 (2016) 172.CrossRefGoogle Scholar
Hummers, W.S., Offeman, R.E., J. Am. Chem. Soc. 80 (1958) 1339-1339.CrossRefGoogle Scholar
Park, S., An, J., Potts, J.R., Velamakanni, A., Murali, S., R.S. Carbon . 49 (2011) 3019-3023.CrossRefGoogle Scholar
Berridge, R., Wright, S.P., Skabara, P.J., Dyer, A., Steckler, T., Argun, A.A., Reynolds, J.R., Harrington, R., Clegg, W., J. Mater. Chem. 17 (2007) 225-231.CrossRefGoogle Scholar
Rittmeyel, S. P., Groß, A., Beilstein J Nanotechnol. 3 (2012) 909919.CrossRefGoogle Scholar
Yuan, Y.X., Peng, H.S., Ping, J.T., Wang, X.H., You, F.T., Biomed Res Int 11 (2015) 245031.Google Scholar
Beyazkilic, P., Yildirim, A., Bayindir, M., Nanoscale 6 (2014) 15203-9.CrossRefGoogle Scholar
Sun, X., Liu, Y., Shaw, G., Carrier, A., Dey, S., Zhao, J., Lei, Y., ACS Appl. Mater. Interfaces 7 (2015) 13189-97.CrossRefGoogle Scholar
Park, S. J., Kim, S., Florence Anjong, T.F., Lee, S.E., Kim, J., Carbon 94 (2015) 448-454.CrossRefGoogle Scholar
Dimitrios, K., Stylianakis, M.M., Stratakis, E., Kymakis, E., J. Colloid Interface Sci. 430 (2014), 430, 108-112.Google Scholar
Rojas-Montoya, S.M., Vonlanthen, M., Porcu, P., Flores-Rojas, G., Ruiu, A., Morales-Morales, D., Rivera, E.. Dalton Transactions 48 (2019), 10435-10447.CrossRefGoogle Scholar