Description of the publication:

Authors:

Iwan, A., Sęk, D., Pociecha, D., Sikora, A., Palewicz, M., Janeczek, H.

Title:

New discotic-shaped azomethines with triphenylamine moieties: Thermal, structural behaviors and opto-electrical properties

Journal:

Journal of Molecular Structure

Year:

2010

Vol:

981 (1-3)

Pages:

120-129

ISSN/ISBN:

00222860

DOI:

10.1016/j.molstruc.2010.07.039

Link:

http://www.sciencedirect.com/science/article/pii/S0379677910003371

Keywords:

Azomethines; Devices; Discotic compounds; Fullerenes; Triphenylamine derivatives

Abstract:

Three discotic-shaped azomethines were prepared by condensation reactions of 4,4',4''-triformyltriphenylamine with various aliphatic monoamines. Their chemical structures were confirmed by FTIR, 1H, 13C NMR spectroscopies, as well as elemental analysis. Thermal properties of the azomethines were examined by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (WAXRD, SAXRD). Moreover, UV-vis properties of the thin films of the compounds were investigated on the quartz substrate without and with [6,6]-phenyl C 61 butyric acid methyl ester (PC61BM). Current-voltage (I-V) measurements were performed on ITO/compound/Al, ITO/compound:PC 61BM/Al and ITO/PEDOT:PSS/compound:PC61BM/Al devices in the dark and during irradiation with light (under illumination 1000 W/m2). Additionally, the compounds were tested using various AFM techniques.

References:

♦ Strohriegl, P., Grazulevicius, J.V., (2002) Adv. Mater., 14, p. 1439
♦ Van Slyke, S.A., Tang, C.W., (1985), US Patent No. 4539507Shirota, Y., (2005) J. Mater. Chem., 15, p. 75
♦ Kim, D.Y., Cho, H.N., Kim, C.Y., (2000) Prog. Polym. Sci., 25, p. 1089
♦ Zhang, X., Li, Z.-C., Li, K.-B., Lin, S., Du, F.-S., Li, F.-M., (2006) Prog. Polym. Sci., 31, p. 893
♦ Lo, S.-C., Burn, P.L., (2007) Chem. Rev., 107, p. 1097
♦ Shirota, Y., Kageyama, H., (2007) Chem. Rev., 107, p. 953
♦ Porres, L., Mongin, O., Katan, C., Charlot, M., Pons, T., Mertz, J., Blanchard-Desce, M., (2004) Org. Lett., 6, p. 47
♦ Wei, P., Bi, X., Wu, Z., Xu, Z., (2005) Org. Lett., 7, p. 3199
♦ Xia, H., He, J., Peng, P., Zhou, Y., Li, Y., Tian, W., (2007) Tetrahedron Lett., 48, p. 5877
♦ Ichikawa, M., Hibino, K., Yokoyama, N., Miki, T., Koyama, T., Taniguchi, Y., (2006) Syn. Met., 156, p. 1383
♦ Kim, Y.K., Hwang, S.-H., (2006) Syn. Met., 156, p. 1028
♦ Lee, J.Y., Park, J.-Y., Min, S.-H., Lee, K.-W., Baek, Y.G., (2007) Thin Solid Film, 515, p. 7726
♦ Sonntag, M., Kreger, K., Hanft, D., Strohriegl, P., Setayesh, S., De Leeuw, D., (2005) Chem. Mater., 17, p. 3031
♦ Kim, M.-J., Seo, E.-M., Vak, D., Kim, D.-Y., (2003) Chem. Mater., 15, p. 4021
♦ He, C., He, Q., Yang, X., Wu, G., Yang, C., Bai, F., Shuai, Z., Li, Y., (2007) J. Phys. Chem. C., 111, p. 8661
♦ Niu, H., Huang, Y., Bai, X., Li, X., Zhang, G., (2004) Mater. Chem. Phys., 86, p. 33
♦ Niu, H.-J., Huang, Y.-D., Bai, X.-D., Li, X., (2004) Mater. Lett., 58, p. 2979
♦ Sęk, D., Iwan, A., Kaczmarczyk, B., Jarz±bek, B., Kasperczyk, J., Bednarski, H., (2007) High Perform. Polym., 19, p. 401
♦ Sęk, D., Iwan, A., Kaczmarczyk, B., Jarz±bek, B., (2007) Mol. Cyst. Liq. Cryst., 468, p. 119
♦ Sęk, D., Iwan, A., Jarz±bek, B., Kaczmarczyk, B., Kasperczyk, J., Mazurak, Z., Domański, M., Łapkowski, M., (2008) Macromolecules, 41, p. 6653
♦ Sęk, D., Iwan, A., Jarz±bek, B., Kaczmarczyk, B., Kasperczyk, J., Janeczek, H., Mazurak, Z., (2009) Spectrochim. Acta A: Mol. Biomol. Spectrosc., 72, p. 1
♦ Liou, G.-S., Lin, H.-Y., Hsieh, Y.-L., Yang, Y.-L., Polym, J., (2007) Sci. A. Polym. Chem., 45, p. 4921
♦ Majumdar, K.C., Pal, N., Debnath, P., Rao, N.V.S., (2007) Tetrahedron Lett., 48, p. 6330
♦ Wang, Y.-J., Sheu, H.-S., Lai, C.K., (2007) Tetrahedron, 63, p. 1695
♦ Yang, C.J., Jenekhe, S.A., (1995) Macromolecules, 28, p. 1180

Example figure:

3D topography view of the A2 azomethine sample.