A novel polyazomethines bearing triphenylamine core and a proper model compound were synthesized and their spectroscopic (FTIR, 1 H NMR) and optical (UV-vis, photoluminescence) properties and also a molecular dynamic calculations were investigated. The polymers which were soluble in organic solvents (chloroform, dimethylacetamide, m-cresol) and formed transparent foils, emitted blue light and their photoluminescence band and intensity were solvent dependent. Additionally, the effects of blending the new polyazomethines with other polymers—PMMA, polyvinylophenol on UV-vis spectra were examined. Non-covalent ionic-type interactions between azomethines and methanesulfonic acid (MSA), m-cresol (MC) and p-chlorophenol (pClp) were also investigated. The structure formation of azomethines complexes are discussed on the basis of 1H NMR and FTIR. Photoluminescence and absorption properties of the azomethines compounds after doping with MSA, MC and pClp were tested.
Kim, D.Y., Cho, H.N., and Kim, C.Y. (2000). Blue Light Emitting Polymers, Prog. Polym. Sc., 25: 1089—1139.
2.
Yu, W.-L. , Pei, J., Huang, W., and Heeger, A.J. (2000). A Novel Triarylamine-Based Conjugated Polymer and its Unusual Light-emitting Properties, Chem. Com., 681—682.
3.
Grigoras, M., Catanescu, O., and Simionescu, C.I. (2001). Polyazomethines, Rev. Roum. Chim., 46: 927—939.
4.
Grigoras, M., and Catanescu, C.O. (2004). Imine Oligomers and Polymers, J Macromol Sci Part C Polym Rev., C44(2):1—37.
5.
Sęk, D. and Iwan, A. (2003). Structure-Properties Relationship Investigations of New Polyketanils, Recent Research Developments in Polymer Science, Transworld Research Network, India, 7: 91—106.
6.
Iwan, A., Sęk, D., Kasperczyk, J., Mazurak, Z., Janeczek, H., Rannou, P., and Proń, A. (2004). Molecular Design of π-Conjugated Poly(ketanil)s with Tunable Spectroscopic Properties, New J. Chem., 28: 1554— 1561.
7.
Iwan, A., Sęk, D. and Kasperczyk, J. (2005). Characterization and Photoluminescence Study of Blue and Green Emitting Polyketanils and Their Blends, Macromolecules , 38: 4384—4392.
8.
Meng, F., Liu, C., Hua, J., Cao, Y., Chen, K., and Tian, H. (2003). Novel Linear and Tri-branched Copolymers Based on Triphenylamine for Non-doping Emitting Materials, Eur. Polym. J., 39: 1325— 1331.
9.
Hua, J.L., Li, B., Meng, F.S., Ding, F.,. Qian, S.X., and Tian, H. (2004). Polymer, 45: 7143—7149.
10.
Meng, F., Mi, J., Qian, S.K., Chen, K., and Tian, H. (2003). Linear and Tri-branched Copolymers for Two-photon Absorption and Two-photon Fluorescent Materials, Polymer, 44: 6851—6855.
11.
He, Q. , Huang, H., Lin, H., Yang, J., and Bai, F. (2003). Synthesis and Characterization of Novel Hyper-branched Oligomer with 1,3,5-trisphenylbenzene as Cores, Synth. Met., 135—136: 165—166.
12.
Pu, Y.-J. , Kurata, T., Soma, M., Kido, J., andNishide. H. (2004). Triphenylamine- and oxadiazole —substituted poly(1,4-phenylene)s: Synthesis, photo- and electroluminescent properties . Synth. Met., 143: 207—214.
13.
Cheng, S-H. , Hsiao, S-H., Su, T-H., and Liou, G-S. (2005). Novel Aromatic Poly(Amine-Imide)s Bearing a Pendent Triphenylamine Group: Synthesis, Thermal, Photophysical, Electrochemical and Electrochromic Characteristics, Macromolecules,38: 307—316.
14.
Niu, H., Huang, Y., Bai, X., Li, X., and Zhang, G. (2004). Study on Crystalization, Thermal Stability and Hole Transport Properties of Conjugated Polyazomethine Materials Containing 4,4'-Bisaminetriphenylamine, Mat. Chem. Phys., 86: 33—37.
15.
Niu, H-J. , Huang, Y-D., Bai, X-D., and Li, X. (2004). Novel Poly-Schiff Bases Containing 4,4'-Diaminotriphenylamine as Hole Transport Material for Organic Electronic Device, Mat. Lett., 58: 2979—2983.
16.
Jenekhe, S.A., Johnson, P.O., and Agrawal, A.K. (1989). Solubilization, Solutions and Processing of Aromatic Heterocyclic Rigid Rod Polymers in Aprotic Organic Solvents: Poly(p-phenylene-2,6-benzobisthiazolediyl) (PBT), Macromolecules, 22: 3216—3222.
17.
Roberts, M.F., and Jenekhe, S.A. (1990). Liquid Crystalline Solutions of Poly(p-phenylene benzobisthiazole), Polym. Commun. , 31: 215—217.
18.
Jenekhe, S.A., and Johnson, P.O. (1990). Complexation-Mediated Solubilization and Processing of Rigid-Chain and Ladder Polymers in Aprotic Organic Solvents, Macromolecules,23: 4419—4429.
19.
Agrawal, A.K., and Jenekhe, S.A. (1992). Thin-film Processing and Optical Properties of Conjugated Rigid-Rod Polyquinolines for Nonlinear Optical Applications, Chem. Mater., 4: 95—104.
20.
Roberts, M.F., and. Jenekhe , S.A. (1994). Lewis Acid Coordination Complexes of Polymers: 3. Poly(benzobisimidazobenzophenanthroline) Ladder and Semiladder Polymers, Polymer, 35: 4313—4325.
21.
Eichen, Y. , Nakhmanovich, G., Gorelik, V., Epshtein, O., Poplawski, J.M., and Ehrenfreund , J. (1998). Effect of Protonation-Deprotonation Processes on the Electrooptical Properties of Bipyridine-Containing Poly(p-phenylene-vinylene), J. Am. Chem. Soc., 120, 10463—10470.
22.
Ruokolainen, J., ten Brinke, G., and Ikkala, O. (1999). Supramolecular Polymeric Materials with Hierarchical Structure—Within-Structure Morphologies , Adv. Mater., 11: 777—780.
23.
Ikkala, O. and ten Brinke, G. (2002). Functional Materials Based on Self-Assembly of Polymeric Supramolecules, Science , 295: 2407—2409.
24.
Polushkin, E. , van Ekenstein, G.A., Dolbnya, I., Bras, W., Ikkala, O., and ten Brinke , G. (2003). In S itu Small Synchrotron X-Ray Scattering Study of Shear-Induced Macroscopic Orientation of Hierarchically Structured Comb-Shaped Supramolecules, Macromolecules, 36: 1421—1423.
25.
Knaapila, M., Ikkala, O., Torkkeli, M., Jokela, K., Serimaa, R., Dolbnya, I.P., Bras, W., Horsburgh, L.E., Pålson, L.O. and Monkman, A.P. (2002). Polarized Luminescence from Self-Assembled, Aligned and Cleaved Supramolecules of Highly Ordered Rodlike Polymers, Appl. Phys. Lett., 81: 1489—1491.
26.
Yang, C-J. and Jenekhe, S.A. (1995). Conjugated Aromatic Polyimines. 2. Synthesis, Structure and Properties of New Aromatic Polyazomethines, Macromolecules,28: 1180—1196
27.
Wang, C., Shieh, S., LeGoff, E. and Kanatzidis, M.G. (1996). Synthesis and Characterization of a New Conjugated Aromatic Poly(azomethine) Derivative Based on the 3'4'-Dibutyl-α-Terthiophene Building Block, Macromolecules, 29: 3147—3156.
28.
Morgan, P.W., Kwolek, S.L. and Pletcher, T.C. (1987). Aromatic Azomethine Polymers and Fibers, Macromolecules,20: 729—739.
29.
Miyaji, T. , Azuma, C., Asaoka, E. And Nakamura, E. (2000). Regeneration of Polycondensation of Wholly Aromatic Poly(azomethine)s with 1,5 or 2,6-Substituted Naphthalene Moiety in Main Chain, J. Polym. Sci. Part A: Polym. Chem., 38: 1064—1072.
30.
Quan, S., Teng, F., Xu, Z., Qian, L., Han, Y., Wang, Y. and Xu, X. (2006). Solvent and Concentration Effects on Fluorscence Emission in MEH-PPV Solution, Eur. Polym. J., 42: 228—233.
31.
MS Modeling v 4.0.0, Accelrys Software Inc .
32.
Delley, B. (1990). An All-Electron Numerical method for Solving the Local Density Functional for Poly-atomic Molecules , J. Chem. Phys., 92: 508—517.
33.
Delley, B. (2000). From Molecules to Solids with the DMol3 Approach, J. Chem. Phys., 113: 7756—7764.
