Description of the publication:

Authors:

Iwan, A., Guimaraes, J.R., Santos, M.C.D., Schab–Balcerzak, E., Krompiec, M., Palewicz, M., Sikora, A.

Title:

Polyazomethine with vinylene and phenantridine moieties in the main chain: Synthesis, characterization, opto(electrical) properties and theoretical calculations

Journal:

High Performance Polymers

Year:

2012

Vol:

24 (4)

Pages:

319–330

ISSN/ISBN:

09540083

DOI:

10.1177/0954008312440470

Link:

http://hip.sagepub.com/content/24/4/319.refs

Keywords:

current density–voltage characteristics; HOMO–LUMO; polyazomethines; theoretical calculations

Abstract:

The opto(electrical) properties and theoretical calculations of polyazomethine with vinylene and phenantridine moieties in the main chain were investigated in the present study. 2,5–Bis(hexyloxy)–1,4–bis[(2,5–bis(hexyloxy)– 4–formyl–phenylenevinylene]benzene was polymerized in solution with 3,8–diamino–6–phenylphenanthridine (PAZ–PV–Ph). The temperatures of 5% weight loss (T5%) of the polyazomethine was observed at 356 °C in nitrogen. Electrochemical properties of thin film of the polymer were studied by differential pulse voltammetry. The HOMO level of the PAZ–PV–Ph was at –4.97 eV. The energy band gap (Eg) was detected of approximately ~1.9 eV. Energy band gap (Eg opt) was additionally calculated from absorption spectrum and absorption coefficient α. The absorption UV–vis spectra of polyazomethine recorded in solution showed a blue shift in comparison with the solid state. HOMO–LUMO levels and Eg were additionally calculated theoretically by density functional theory and molecular simulations of PAZ–PV–Ph are presented. Current density–voltage (J–U) measurements were performed on ITO/PAZ–PV–Ph/Al, ITO/TiO2/PAZ–PV–Ph/Al and ITO/PEDOT/PAZ–PV–Ph:TiO2/Al devices in the dark and during irradiation with light (under illumination of 1000 W/m2). The polymer was tested using AFM technique and roughness (Ra, Rms) along with skew and kurtosis are presented.

References:

♦ Iwan, A., Sęk, D., Processible polyazomethines and polyketanils: From aerospace to light–emitting diodes and other advanced applications (2008) Progress in Polymer Science (Oxford), 33 (3), pp. 289–345., DOI 10.1016/j.progpolymsci.2007.09.005, PII S007967000700113X
♦ Niu, H., Huang, Y., Bai, X., Study on crystallization, thermal stability and hole transport properties of conjugated polyazomethine materials containing 4,4'–bisamine–triphenylamine (2004) Mater Chem Phys, 86, pp. 33–37
♦ Niu, H.–J., Huang, Y.–D., Bai, X.–D., Novel poly–Schiff bases containing 4,4'–diamino–triphenylamine as hole transport material for organic electronic device (2004) Mater Lett, 58, pp. 2979–2983
♦ Sęk, D., Jarz±bek, B., Grabiec, E., A study of thermal, optical and electrical properties of new branched triphenylamine–based polyazomethines (2010) Synth Met, 160, pp. 206–2076
♦ Sęk, D., Iwan, A., Kaczmarczyk, B., Jarz±bek, B., Supramolecular modification of optical properties of some new polyazomethines (2007) Molecular Crystals and Liquid Crystals, 468 (1), pp. 119–129., DOI 10.1080/15421400701229719, PII 783015597
♦ Sęk, D., Iwan, A., Jarz±bek, B., Hole transport triphenylamine–azomethine conjugated system: Synthesis and optical, photoluminescence and electrochemical properties (2008) Macromolecules, 41, pp. 6653–6663
♦ Sęk, D., Iwan, A., Jarz±bek, B., Characterization and optical properties of oligoazomethines with triphenylamine moieties exhibiting blue, blue–green and green light (2009) Spectrochim Acta Part A: Mol Biomol Spectrosc, 72, pp. 1–10
♦ Liou, G.–S., Lin, H.–Y., Hsieh, Y.–L., Yang, Y.–L., Synthesis and characterization of wholly aromatic poly(azomethine)s containing donor – Acceptor triphenylamine moieties (2007) Journal of Polymer Science, Part A: Polymer Chemistry, 45 (21), pp. 4921–4932., DOI 10.1002/pola.22228
♦ Hindson, J.C., Ulgut, B., Friend, R.H., All–aromatic liquid crystal triphenylamine–based poly(azomethine)s as hole transport materials for opto–electronic applications (2010) J Mater Chem, 20, pp. 937–944
♦ Iwan, A., Palewicz, M., Sikora, A., Aliphatic–aromatic poly(azomethine)s with ester groups as thermotropic materials for opto(electronic) applications (2010) Synth Met, 160, pp. 1856–1867
♦ Iwan, A., Schab–Balcerzak, E., Pociecha, D., Characterization, liquid crystalline behavior, electrochemical and optoelectrical properties of new poly(azomethine)s and poly(imide) with siloxane linkages (2011) Opt Mater, 34, pp. 61–74; Rohlfing, F., Ddc, B., Non–linear Stark effect in polyazomethine and poly(p–phenylene–vinylene): The interconnection of chemical and electronic structure (1998) Chem Phys, 227, pp. 133–151
♦ Iwan, A., Mazurak, Z., Kaczmarczyk, B., Jarz±bek, B., Sęk, D., Synthesis and characterization of polyketanils with 3,8–diamino–6– phenylphenanthridine moieties exhibiting light emitting properties. Molecular and supramolecular engineering concept (2008) Spectrochimica Acta – Part A: Molecular and Biomolecular Spectroscopy, 69 (2), pp. 291–303., DOI 10.1016/j.saa.2007.04.001, PII S1386142507001874
♦ Iwan, A., Kaczmarczyk, B., Jarz±bek, B., Influence of long–chain aliphatic dopants on the spectroscopic properties of polyketimine containing 3,8–diamino–6–phenylphenanthridine and ethylene linkage in the main chain. Noncovalent interaction: Proton transfer, hydrogen and halogen bonding (2008) Phys Chem A, 112, pp. 7556–7566
♦ Cimecioglut, A.L., Weiss, R.A., Aromatic polyamides of 3,8–diamino–6–phenylphenanthridina end their molecular complexes with sulfonated polystyrene ionomers (1995) Macromolecules, 28, pp. 6343–6346
♦ Becke, A.D., (1993) J Chem Phys, pp. 5648–5652
♦ Frisch, M.J., Trucks, G.W., Schlegel, H.B., (2004) Gaussian 03, Revision E1
♦ Sęk, D., Kaczmarczyk, B., Jarz±bek, B., (2007) Nowe Fotoluminescencyjne Poliazometiny. Modyfikacja Polimerow. Stan i Perspektywy W Roku 2007, pp. 307–310., Wroclaw, Poland: Wydział Chemiczny Politechniki Wrocławskiej;
♦ Yang, C.J., Jenekhe, S.A., Conjugated aromatic polyimines. 2. Synthesis, structure and properties of new aromatic polyazomethines (1995) Macromolecules, 28, pp. 1180–1196;
♦ Rusu, G.I., Airinei, A., Rusu, M., Prepelita, P., Marin, L., Cozan, V., Rusu, I.I., On the electronic transport mechanism in thin films of some new poly(azomethine sulfone)s (2007) Acta Materialia, 55 (2), pp. 433–442., DOI 10.1016/j.actamat.2006.07.048, PII S1359645406006136
♦ Jarz±bek, B., Weszka, J., Burian, A., Pocztowski, G., Optical properties of amorphous thin films of the Zn–P system (1996) Thin Solid Films, 279 (1–2), pp. 204–208
♦ Gierschner, J., Cornil, J., Egelhaaf, H.J., Optical bandgaps of γ-conjugated organic materials at the polymer limit: Experiment and theory (2007) Advanced Materials, 19 (2), pp. 173–191., DOI 10.1002/adma.200600277
♦ Masui, M., Ohmori, H., Anodic oxidation of Schiff bases. Part I. Oxidation of N–benzylidene–p–anisidines in acetonitrile (1972) J Chem Soc Perkin Trans, 2, pp. 1882–1887
♦ Li, Y., Cao, Y., Gao, J., Electrochemical properties of luminescent polymers and polymer light–emitting electrochemical cells (1999) Synth Met, 99, pp. 243–248
♦ Pommerehne, J., Vestbeber, H., Guss, W., Efficient two layer leds on a polymer blend basis (1995) Adv Mater, 7, pp. 551–554;
♦ Root, D.K., Smith, W.H., Electrochemical behavior of selected imine derivatives, reductive carboxylation, alpha–amino acid synthesis (1982) J Electrochem Soc, 129, pp. 1231–1236
♦ Freire, M.G., Neves, C.M.S.S., Marrucho, I.M., Hydrolysis of tetrafluoroborate and hexafluorophosphate counter ions in imidazolium–based ionic liquids (2010) J Phys Chem A, 114, pp. 3744–3749
♦ Gebala, A.E., Jones, M.M., A rate study of the hydrolysis of the hydroxypentafluoroarsenate(V) anion (1969) J Inorg Nucl Chem, 31, pp. 771–776
♦ Lupton, J.M., Single–molecule spectroscopy for plastic electronics: Materials analysis from the bottom–up (2010) Adv Mater, 22, pp. 1689–1721
♦ Becker, K., Da Como, E., Feldmann, J., How chromophore shape determines the spectroscopy of phenylene–vinylenes: Origin of spectral broadening in the absence of aggregation (2008) J Phys Chem B Lett, 112, pp. 4859–4864
♦ Kemerink, M., Van Duren, J.K.J., Jonkheijm, P., Pasveer, W.F., Koenraad, P.M., Janssen, R.A.J., Salemink, H.W.M., Wolter, J.H., Relating substitution to single–chain conformation and aggregation in Poly(p–phenylene Vinylene) films (2003) Nano Letters, 3 (9), pp. 1191–1196., DOI 10.1021/nl034317j
♦ Wijsboom, Y.H., Sheynin, Y., Patra, A., Tuning of electronic properties and rigidity in PEDOT analogs (2011) J Mater Chem, 21, pp. 1368–1372
♦ Hreniak, A., Nyk, M., Hreniak, D., Optical property, nanocrystalline films, synthesis of europium (2004) Materials Science–Poland, 22, pp. 227–234
♦ Mukherjee, B., Karthik, C., Ravishankar, N., Hybrid sol–gel combustion synthesis of nanoporous anatase (2009) J Phys Chem C, 113, pp. 18204–18211
♦ Nolan, T.N., Seery, M.K., Pillai, S.C., Spectroscopic investigation of the anatase–to–rutile transformation of sol–gel–synthesized TiO2 photocatalysts (2009) J Phys Chem C, 113, pp. 16151–16157
♦ Yan, W., Mahurin, S.M., Overbury, S.H., Dai, S., Nonhydrolytic layer–by–layer surface sol–gel modification of powdered mesoporous silica materials with TiO 2 (2005) Chemistry of Materials, 17 (8), pp. 1923–1925., DOI 10.1021/cm048118s

Example figure:

3D topography view of the PAZ-PV-Ph sample.