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Towards the Synthesis of Mono- and Bi-Functional Amphiphilic Oligothiophenes: Organic Materials for Opto-Electronic Applications

Published online by Cambridge University Press:  10 February 2011

R.C. Advincula ,
S. Inaoka ,
M. Park ,
D. Phillips  and
D.M. Shin
R.C. Advincula
Affiliation:
Department of Chemistry, University of Alabama at Birmingham, Chemistry Building, Birmingham, AL 35294-1240, USA
S. Inaoka
Affiliation:
Department of Chemistry, University of Alabama at Birmingham, Chemistry Building, Birmingham, AL 35294-1240, USA
M. Park
Affiliation:
Department of Chemistry, University of Alabama at Birmingham, Chemistry Building, Birmingham, AL 35294-1240, USA Department of Chemical Engineering, Hong-Ik University, Seoul, Korea
D. Phillips
Affiliation:
Department of Chemistry, University of Alabama at Birmingham, Chemistry Building, Birmingham, AL 35294-1240, USA
D.M. Shin
Affiliation:
Department of Chemical Engineering, Hong-Ik University, Seoul, Korea
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Abstract

In this report, we describe our initial synthesis and characterization of mono-functional and bi-functional dibromoalkyl oligothiophenes to achieve amphiphilicity and telechelic functionality. Oligothiophenes are an important class of organic materials for opto-electronic devices and display applications. We have mono-functionalized oligothiophenes by the synthesis of a quinquethiophene bromoalkyl derivative. A bi-functional sexithiophene was derived primarily by the symmetrical coupling of terthiophene derivatives. Both were synthesized using Grignard coupling and lithiation reaction methodologies. UV-Vis, IR, NMR, MALDI-TOF-MS, and DSC confirmed the structure and physical properties of the oligomers. In addition, we have also synthesized an amphiphilic diamine derivative from the reaction of hexamethylenediamine with a bromoalkyl terthiophene derivative. Using photoluminescence, the photophysical properties of the oligomers were found to be that of typical oligothiophenes. Processing as ultrathin films for devices is currently being investigated.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 561: Symposium F – Organic Nonlinear Optical Materials and Devices , 1999 , 155
Copyright
Copyright © Materials Research Society 1999

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References

REFERENCES

[1] Lovinger, A., Davis, D., Dodabalapur, A., Katz, H., Chem. Mater. 8, 2836 (1996).Google Scholar
[2] Servet, B., Horowitz, G., Ries, S., Lagorsse, O., Alnot, P., Yassar, A., Deloffre, F., Srivastava, P., Hajlaoui, R., Lang, P., Gamier, F., Chem. Mater. 6, 1809 (1994).Google Scholar
[3] Gamier, F., Yassar, A., Hajlaoui, R., Horowitz, G., Deloffre, F., Servet, B., Ries, S., Alnot, P., J. Am. Chem. Soc. 115, 8716 (1993).Google Scholar
[4] Horowitz, G., Gamier, F., Yassar, A., Hajlaoui, R., Kouki, F. Adv. Mater. 8, 52 (1996).Google Scholar
[5] Cacialli, F., Marks, R., Friend, R., Zamboni, R., Taliani, C., Maratti, S., Holmes, A., Synth. Met. 76, 145 (1996).Google Scholar
[6] Leeuw, D. de, Lous, E.J., Synth. Met. 65, 45 (1994).Google Scholar
[7] Ulman, A., Ultrathin Organic Films, (Academic Press: San Diego, 1991).Google Scholar
[8] Electrical, Optical, and Magnetic Properties of Organic Solid-State Materials IV. Eds. Reynolds, J., Jen, A.K., Rubner, M., Chiang, L. and Dalton, L., MRS Proceedings, (MRS, Pennsylvania, Vol. 488, 1998).Google Scholar
[9] Mullen, K., Lex, J., Schulz, R., Wakter, F., Polymer Bull. 24, 263 (1990); G. Hochberg, R. Schultz, Polymer Intl. 32, 309 (1993).Google Scholar
[10] Park, M., Shin, D., Inaoka, S., Advincula, R., manuscript in preparation.Google Scholar
[11] Sease, J., and Zechmeister, L., J. Am. Chem. Soc. 69, 270 (1947).Google Scholar
[12] Katz, H., Dodabalapur, A., Torsi, L., Lovinger, A., and Ruel, R., Polym. Mat. Sci. Eng. Preprints, 72, 467 (1995).Google Scholar
[13] Michalitsch, R., Lang, P., Yassar, A., Nauer, G., Gamier, F., Adv. Mater. 9, 321 (1997).Google Scholar