Polymer-Controlled Synthesis of 1-(2-Pyridylazo)-2-Naphthol Hierarchical Architectures
Jie Leng, Qiulin Liao, Yong Gao, Huaming Li
DOI: 10.4236/msa.2011.26074   PDF   HTML     5,295 Downloads   9,120 Views   Citations


The self-assembly of organic 1-(2-pyridylazo)-2-naphthol (PAN) into hierarchical architectures, such as microfibers, microrods, and sheaflike structures, in solution was successfully achieved by reprecipitation method with the assistance of thermoresponsive diblock copolymer poly(N,N-dimethylacrylamide)-b-poly(N-isopropylacrylamide) (PDMA-b-PNIPAM). It was found that the morphology modification can be readily controlled by varying the polymer concentrations. The optical absorption and fluorescence emission properties of the as-prepared PAN architectures were investigated. Time-dependent spectra of the precipitating solution for sheaflike structures formation were measured to monitor the self-assembly process of PAN molecules. The results showed that the PAN microstructures exhibited intense fluorescence emission, indicating an unusual aggregation-induced emission enhancement (AIEE) phenomenon for PAN, which have great potential for future use in optoelectronic microdevices.

Share and Cite:

J. Leng, Q. Liao, Y. Gao and H. Li, "Polymer-Controlled Synthesis of 1-(2-Pyridylazo)-2-Naphthol Hierarchical Architectures," Materials Sciences and Applications, Vol. 2 No. 6, 2011, pp. 555-563. doi: 10.4236/msa.2011.26074.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] D. Horn and J. Rieger, “Organic nanoparticles in the aqueous phase-theory, experiment, and use,” Angew. Chem. Int. Ed., Vol. 40, No. 23, 2001, pp. 4330-4361.
[2] F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, and A. P. H. J. Schenning, “About supramolecular assemblies of π-conjugated systems,” Chem. Rev., Vol. 105, No. 4, 2005, pp. 1491-1546.
[3] Y. S. Zhao, H. Fu, A. Peng, Y. Ma, D. Xiao, and J. Yao, “Low-dimensional nanomaterials based on small organic molecules: preparation and optoelectronic properties,” Adv. Mater., Vol. 20, No. 15, 2008, pp. 2859-2876.
[4] Q. Tang, L. Jiang, Y. Tong, H. Li, Y. Liu, Z. Wang, W. Hu, Y. Liu, and D. Zhu, “Micrometer- and nanometer-sized organic single-crystalline transistors,” Adv. Mater., Vol. 20, No. 15, 2008, pp. 2947-2951.
[5] S. Cui, H. Liu, L. Gan, Y. Li, and D. Zhu, “Fabrication of low-dimension nanostructures based on organic conjugated molecules,” Adv. Mater., Vol. 20, No. 15, 2008, pp. 2918-2925.
[6] F. Bertorelle, D. Lavabre, and S. Fery-Forgues, “Dendrimer-tuned formation of luminescent organic microcrystals,” J. Am. Chem. Soc., Vol. 125, No. 20, 2003, pp. 6244-6253.
[7] Y. S. Zhao, H. Fu, A. Peng, Y. Ma, Q. Liao, and J. Yao, “Construction and optoelectronic properties of organic one-dimensional nanostructures,” Acc. Chem. Res., Vol. 43, No. 3, 2009, pp. 409-418.
[8] M. Abyan, F. Bertorelle, and S. Fery-Forgues, “Use of linear polymers to control the preparation of luminescent organic microcrystals,” Langmuir, Vol. 21, No. 13, 2005, pp. 6030-6037.
[9] L. B?rlǎ, F. Bertorelle, F. Rodrigues, S. Badré, R. Pansu, and S. Fery-Forgues, “Effects of DNA on the growth and optical properties of luminescent organic microcrystals,” Langmuir, Vol. 22, No. 14, 2006, pp. 6256-6265.
[10] H. B. Fu and J. N.Yao, “Size effects on the optical properties of organic nanoparticles,” J. Am. Chem. Soc., Vol. 123, No. 7, 2001, pp. 1434-1439.
[11] D. Xiao, L. Xi, W. Yang, H. Fu, Z. Shuai, Y. Fang, and J. Yao, “Size-tunable emission from 1,3-diphenyl-5-(2- anthryl)-2-pyrazoline nanoparticles,” J. Am. Chem. Soc., Vol. 125, No. 22, 2003, pp. 6740-6745.
[12] C. F. J. Faul and M. Antonietti, “Facile synthesis of optically functional, highly organized nanostructures: dye- surfactant complexes,” Chem. - Eur. J., Vol. 8, No. 12, 2002, pp. 2764-2768.
[13] A. Taden, K. Landfester, and M. Antonietti, “Crystallization of dyes by directed aggregation of colloidal intermediates: a model case,” Langmuir, Vol. 20, No. 3, 2004, pp. 957-961.
[14] H. P. Cong and S. H. Yu, “Recrystallization and shape control of crystals of the organic dye acid green 27 in a mixed solvent,” Chem. - Eur. J., Vol. 13, No. 5, 2007, pp. 1533-1538.
[15] T. K. Zhang, J. H. Zhu, H. B. Yao, and S. H. Yu, “Novel fluorescein hierarchical structures fabricated by recrystallization under control of polyelectrolytes,” Cryst. Growth Des., Vol. 7, No. 12, 2007, pp. 2419-2428.
[16] Y. Wang, H. Fu, A. Peng, Y. S. Zhao, D. Xiao, J. Ma, Y. Ma, and J. Yao, “Distinct nanostructures from isomeric molecules of bis(iminopyrrole) benzenes: effects of molecular structures on nanostructural morphologies,” Chem. Commun., 2007, pp. 1623-1625.
[17] Y. Gao, X. Zhang, C. Ma, X. Li, and J. Jiang, “Morphology-controlled self-assembled nanostructures of 5,15- di[4-(5-acetylsulfanylpentyloxy)phenyl]porphyrin derivatives. Effect of metal-ligand coordination bonding on tuning the intermolecular interaction,” J. Am. Chem. Soc., Vol. 130, No. 50, 2008, pp. 17044-17052.
[18] X. J. Zhang, X. H. Zhang, K. Zou, C. S. Lee, and S. T. Lee, “Single-crystal nanoribbons, nanotubes, and nanowires from intramolecular charge-transfer organic molecules,” J. Am. Chem. Soc., Vol. 129, No. 12, 2007, pp. 3527-3532.
[19] H. Yu and L. Qi, “Polymer-assisted crystallization and optical properties of uniform microrods of organic dye sudan II,” Langmuir, Vol. 25, No. 12, 2009, pp. 6781- 6786.
[20] R. O. Al-Kaysi, A. M. Müller, T. S. Ahn, S. Lee, and C. J. Bardeen, “Effects of sonication on the size and crystallinity of stable zwitterionic organic nanoparticles formed by reprecipitation in water,” Langmuir, Vol. 21, No. 17, 2005, pp. 7990-7994.
[21] H. Jiang, X. Sun, M. Huang, Y. Wang, D. Li, and S. Dong, “Rapid self-assembly of oligo(o-phenylenediamine) into one-dimensional structures through a facile reprecipitation route,” Langmuir, Vol. 22, No. 7, 2006, pp. 3358-3361.
[22] M. Kastler, W. Pisula, D. Wasserfallen, T. Pakula, and K. Müllen, “Influence of alkyl substituents on the solution- and surface-organization of hexa-peri-hexabenzocoronenes,” J. Am. Chem. Soc., Vol. 127, No. 12, 2005, pp. 4286-4296.
[23] Y. S. Zhao, C. Di, W. Yang, G. Yu, Y. Liu, and J. Yao, “Photoluminescence and electroluminescence from tris (8-hydroxyquinoline)aluminum nanowires prepared by adsorbent-assisted physical vapor deposition,” Adv. Funct. Mater., Vol. 16, No. 15, 2006, pp. 1985-1991.
[24] H. Fu, D. Xiao, J. Yao, and G. Yang, “Nanofibers of 1,3-diphenyl-2-pyrazoline induced by cetyltrimethylammonium bBromide micelles,” Angew. Chem. Int. Ed., Vol. 42, No. 25, 2003, pp. 2883-2886.
[25] J. K. Lee, W. K. Koh, W. S. Chae and Y. R. Kim, “Novel synthesis of organic nanowires and their optical properties,” Chem. Commun., 2002, pp. 138-139.
[26] L. Jiang, Y. Fu, H. Li, and W. Hu, “Single-crystalline, size, and orientation controllable nanowires and ultralong microwires of organic semiconductor with strong photoswitching property,” J. Am. Chem. Soc., Vol. 130, No. 12, 2008, pp. 3937-3941.
[27] E. V. Keuren, E. Georgieva, and J. Adrian, “Kinetics of the formation of organic molecular nanocrystals,” Nano Lett., Vol. 1, No. 3, 2001, pp. 141-144.
[28] H. Kasai, H. S. Nalwa, H. Oikawa, S. Okada, H. Matsuda, N. Minami, A. Kakuta, K. Ono, A. Mukoh, and H. Nakanishi, “A novel preparation method of organic microcrystals,” Jpn. J. Appl. Phys., Vol. 31, 1992, pp. 1132-1134.
[29] X. Zhang, X. Zhang, W. Shi, X. Meng, C. Lee, and S. Lee, “Morphology-controllable synthesis of pyrene nanostructures and its morphology dependence of optical properties,” J. Phys. Chem. B, Vol. 109, No. 40, 2005, pp. 18777-18780.
[30] S. J. Lee, J. T. Hupp, and S. T. Nguyen, “Growth of narrowly dispersed porphyrin nanowires and their hierarchical assembly into macroscopic columns,” J. Am. Chem. Soc., Vol. 130, No. 30, 2008, pp. 9632-9633.
[31] J. Liu, Z. Nie, Y Gao, A. Adronov and H. Li, “ “Click” coupling between alkyne-decorated multiwalled carbon nanotubes and reactive PDMA-PNIPAM micelles,” J. Polym. Sci. A, Vol. 46, No. 21, 2008, pp. 7187-7199.
[32] R. G. Anderson and G. Nickless, “Heterocyclic azo dyestuffs in analytical chemistry. A review,” Analyst, Vol. 92, 1967, pp. 207-238.
[33] J. Gao, B. Peng, H. Fan, J. Kang and X. Wang, “Spectrophotometric determination of palladium after solid-liquid extraction with 1-(2-Pyridylazo)-2-naphthol at 90?C,” Talanta, Vol. 44, No. 5, 1997, pp. 837-842.
[34] A. K. De, R. A. Chalmers, and S. M. Khopkar, “Solvent extraction of metals,” Van Nostrand Reinhold, London, 1970.
[35] H. Faghihian, A. Hajishabani, S. Dadfarnia, and H. Zamani, “Use of clinoptilolite loaded with 1-(2-pyridylazo)-2-naphthol as a sorbent for preconcentration of Pb(II), Ni(II), Cd(II) and Cu(II) prior to their determination by flame atomic absorption spectroscopy,” Int. J. Environ. An. Ch., Vol. 89, No. 4, 2009, pp. 223-231.
[36] S. Shibata, “Solvent extraction and spectrophotometric determination of metals with 1-(2-pyridylazo)-2-naphthol,” Anal. Chim. Acta, Vol. 25, No. 4, 1961, pp. 348-359.
[37] A. J. Convertine, B. S. Lokitz, Y. Vasileva, L. J. Myrick, C. W. Scales, A. B. Lowe, and C. L. McCormick, “Direct synthesis of thermally responsive DMA/NIPAM diblock and DMA/NIPAM/DMA triblock copolymers via aqueous, room temperature RAFT polymerization,” Macromolecules, Vol. 39, No. 5, 2006, pp. 1724-1730.
[38] E. C. Cho, J. Lee, and K. Cho, “Role of bound water and hydrophobic interaction in phase transition of Poly (N-isopropylacrylamide) Aqueous Solution,” Macromolecules, Vol. 36, No. 26, 2003, pp. 9929-9934.
[39] M. Heskins and J. E. Guillet, “Solution properties of poly(N-isopropylacrylamide),” J. Macromol. Sci. A, Vol. 2, No. 8, 1968, pp. 1441-1455.
[40] Z. Wang, K. J. Ho, C. J. Medforth, and J. A. Shelnutt, “Porphyrin nanofiber bundles from phase-transfer ionic self-assembly and their photocatalytic self-metallization,” Adv. Mater., Vol. 18, No. 19, 2006, pp. 2557-2560.
[41] S. J. Lee, C. D. Malliakas, M. G. Kanatzidis, J. T. Hupp, and S. T. Nguyen, “Amphiphilic porphyrin nanocrystals: morphology tuning and hierarchical assembly,” Adv. Mater., Vol. 20, No. 18, 2008, pp. 3543-3549.
[42] L. Kang, Z. Wang, Z. Cao, Y. Ma, H. Fu, and J. Yao, “Colloid chemical reaction route to the preparation of nearly monodispersed perylene nanoparticles: size-tunable synthesis and three-dimensional self-organization,” J. Am. Chem. Soc., Vol. 129, No. 23, 2007, pp. 7305-7312.
[43] H. Shi, L. Qi, J. Ma, and H. Cheng, “Polymer-directed synthesis of penniform BaWO4 nanostructures in reverse micelles,” J. Am. Chem. Soc., Vol. 125, No. 12, 2003, pp. 3450-3451.
[44] J. Xu, X. Liu, J. Lv, M. Zhu, C. Huang, W. Zhou, X. Yin, H. Liu, Y. Li, and J. Ye, “Morphology transition and aggregation-induced emission of an intramolecular charge- transfer compound,” Langmuir, Vol. 24, No. 8, 2008, pp. 4231-4237.
[45] Y. Dong, J. W. Y. Lam, A. Qin, J. X. Sun, J. Z. Liu, Z. Li, J. Z. Sun, H. H. Y. Sung, I. D. Williams, and H. S. Kwok, “Aggregation-induced and crystallization-enhanced emissions of 1,2-diphenyl-3,4-bis(diphenylmethylene)-1- cyclobutene,” Chem. Commun., 2007, pp. 3255-3257.
[46] J. Luo, Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu, H. S. Kwok, X. Zhan, Y. Liu, D. Zhu, and B. Z. Tang, “Aggregation-induced emission of 1-methyl-1,2,3,4,5- pentaphenylsilole,” Chem. Commun., 2001, pp. 1740- 1741.

Copyright © 2022 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.