Synthesis and Surface Properties of a Novel Switchable Bolaform Surfactant

Abstract:

A kind of the ionic bolaform surfactant was synthesized in four steps, with 4-nitrotoluene as raw materials. Firstly, bis-(2-methyl-4-nitrophenyl)-methane (BMNM) was synthesized using paraformaldehyde as a coupling agent; then, bis-(2-methyl-4-aminophenyl) methane BMAM) was obtained through a reduction reaction of BMNM; in the following step, bis-(2-methyl-4-p-hydroxy- azophenyl)methane was prepared through diazotization-coupling reaction; at last, Bolaform surfactant was obtained through a addition reaction of butane sultone and bis-(2-methyl-4-p- hydroxy-azophenyl)methane. The products were characterized by IR and 1HNMR. The surface tension and UV-Vis absorption and fluorescence spectra of aqueous solution of this Bolaform surfactant were tested. The cis/trans photoisomerization of Bolaform surfactants were studied in DMSO solution at 365nm irradiation, which indicate this Bolaform surfactantis photosentive and easily to control surface activity by photoisomerization.

• Periodical: Advanced Materials Research (Volumes 415-417)
• Pages: 1447-1450
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.415-417.1447
• Online since: December 2011
• Authors: Ke Liang Zhang, Ning Sheng Zhang, Chen Tun Qu
• Keywords: Azobenzene, Bolaform, Photoisomerization, Sulfonate Surfactant

References

[1] Pack D W, Putnam D, Langer R., Biotech Bioeng, 67: 217-223 (2000).

[2] Lee E S, Shin H J, J Control Release, 90: 363-374 (2003).

[3] Sa JIT, Hoshno K, Aoyaguz S, J Am Chem Soc, 107: 6865-6868 (1985).

[4] Kakizaw A W, Sakajh, Nishiyam A K, et al., Langmuir, 12: 921-924 (1996).

[5] Kakizaw A W, Sakajh, Nishiyam A K, et al., Langmuir, 17: 8044-8048 (2001).

[6] Aydogann A N., Langmuir, 17: 5703-5706 (2001).

[7] Karthaus O, Shmomura M, Hiokim, et al., J Am Chem Soc, 118: 9174-9175 (1996).

[8] Insun K, John F R, Pieter S, et al., Colloids and Surfaces A: Physicochemical and Engineeering Aspects, 171: 167-174 (2000).

[9] Shin J Y, Abott N L. Langmuir, 15: 4404-4410 (1999).

[10] Liu Y, Jessop P G, Cunningham M, et al., Science, 313: 958-960 (2006).

[11] Dexteb A F, Malcolm A S, Middelberg Anton P J., Nature Materials, 5: 502-506 (2006).

[12] Dalia Abdallah, Matthew J. Cully, Yuzhuo Li., Colloid Polym Sci., 286: 739-745 (2008).

[13] Sakai Hideki, Matsumura Atsutoshi, Yokoyama Shoko et al., Journal of Physical Chemistry B, 103(49): 10737-10740 (1999).

[14] Yan Y, Xiong W, Huang J, Li Z et al., J Phys Chem B, 109: 357-364 (2005).

[15] Qu Jian-Qiang, Wang De-Qiu, Han Fu-She et al., Chemical Research In Chinese Universities, 12: 1939-1943 (2000).

[16] De S, Das S, Girigoswami A., Spectrochimica Acta Part 61: 1821 (2006).

[17] Alexey B, Valery S, Vera H, et al, Monatsh Chem, 140: 789-799 (2009).