Photoisomerization behavior of photochromic amide-based azobenzene dyes exhibiting H-bonding effect: Synthesis and characterization

Gurumurthy Hegde; Yuvaraj Aralapura Rajkumar; Gan Siew Mei; Syed Mahmood; Uttam Kumar Mandal; Achalkumar Ammathnadu Sudhakar

Korean Journal of Chemical Engineering, Vol.33, No.4, 1480-1488, April, 2016

DOI10.1007/s11814-015-0259-8 Export Citation

Photoisomerization behavior of photochromic amide-based azobenzene dyes exhibiting H-bonding effect: Synthesis and characterization

Gurumurthy Hegde^†, Yuvaraj Aralapura Rajkumar¹, Gan Siew Mei¹, Syed Mahmood², Uttam Kumar Mandal², and Achalkumar Ammathnadu Sudhakar³

BMS R and D Centre, BMS College of Engineering, Basavanagudi, Bangalore 560019, India
¹Faculty of Industrial Sciences and Technology, University Malaysia Pahang, 26300, Gambang, Kuantan, Malaysia
²Department of Pharmaceutical, Technology, Kulliyyah of Pharmacy, International Islamic University, Malaysia (IIUM), Pahang Darul Makmur, Malaysia
³Department of Chemistry, Indian Institute of Technology, Guwahati, 781039, Guwahati - Assam, India

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Amide linkage was introduced into azo compound at para position and its optical storage properties were investigated. Synthesized compounds showed liquid crystalline behavior when electron withdrawing group was inserted in the chemical structure. UV/Vis study showed that the photoisomerization effect in solution occurred at 18-24 sec (E-Z) and 5-11 hours (Z-E), whereas in solids it occurred at 30 sec (E-Z) and 5 hours (Z-E). Photoisomerization effect of amide based azodyes in the presence of hydrogen bonding is discussed for the first time. Effect of terminal electronic withdrawing groups on hydrogen bonding is speculated to be the reason behind the surprising behavior. Strong evidence for the structure property relations reported here is useful for applications such as optical storage device in which one can tune the structure according to one’s requirement.

Keywords:Azobenzene;Amide;Hydrogen Bond;Optical Properties;Photoisomerization

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[2] Zhang Z, Xu H, Zheng C, Korean J. Chem. Eng., 30(12), 2219 (2013)

[3] Gan SM, Pearl ZF, Yuvaraj AR, Lutfor MR, Gurumurthy H, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 149, 875 (2015)

[4] Yuvaraj AR, Chan TNW, Yit PG, Gurumurthy H, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 135, 1115 (2014)

[5] Gan SM, Yuvaraj AR, Lutfor MR, Mashitah MY, Gurumurthy H, RSC Adv., 5(9), 6279 (2015)

[6] Bandara HMD, Burdette SC, Chem. Soc. Rev., 41, 1809 (2012)

[7] Iriepa CG, Marazzi M, Frutos LM, Sampedro D, RSC Adv., 3, 6241 (2013)

[8] Beharry AA, Woolley GA, Chem. Soc. Rev., 40, 4422 (2011)

[9] Rau H, “Photoisomerization of Azobenzenes,” In: Rabek JF (Ed):Photochemistry and Photophysic, CRC Press, Boca Raton, 2, 119 (1990).

[10] Li Z, Dong Z, Jiabao W, Biao C, Haiqing L, Carbohydr. Polym., 99, 748 (2013)

[11] Lv JA, Wang WR, Xu JX, Ikeda T, Yu YL, Macromol. Rapid Commun., 35(14), 1266 (2014)

[12] Yu Z, Hecht S, Gesel J, Angew. Chem.-Int. Edit., 52, 13740 (2013)

[13] Ishikawa D, Ito E, Han MN, Hara M, Langmuir, 29(14), 4622 (2013)

[14] Fernandez R, Mondragon I, Rafaela CS, Felippe JP, Osvaldo NOJ, Oyanguren P, Galante MJ, Mater. Sci. Eng. C-Biomimetic Supramol. Syst., 33, 1403 (2013)

[15] Rahman ML, Yusoff MM, Hegde G, Malek MNFA, Samah NA, Srinivasa HT, Kumar S, J. Chinese Chem. Soc., 61(5), 571 (2014)

[16] Dong R, Zhu B, Zhou Y, Yan D, Zhu X, J. Polym. Sci. A: Polym. Chem., 4, 912 (2013)

[17] Yun WD, Wang J, Zhang DW, Li ZT, Science China Chemistry, 55, 2018 (2012)

[18] Balamurugan S, Yeap GY, Mahmood WAK, Tan PL, Cheong KY, J. Photochem. Photobiol. A-Chem., 278, 19 (2014)

[19] Binzet G, Florke U, Kulcu N, Arslan, Act. Cryst., 65, 427 (2009)

[20] Bautista AD, Appelbaum JS, Craig CJ, Michel J, Schepartz A, J. Am. Chem. Soc., 132(9), 2904 (2010)

[21] Gowda BT, Foro S, Fuess H, Act. Cryst., 64, 419 (2008)

[22] Gowda BT, Foro S, Suchetan PA, Fuess H, Terao H, Act. Cryst., E65, 01998 (2009)

[23] Yuvaraj AR, Gan SW, Ajaykumar K, Yusoff MM, Gurumurthy H, RSC Adv., 4, 50811 (2014)

[24] Reddy GNM, Kumar MV, Row TNG, Suryaprakash N, Phys. Chem. Chem. Phys., 12, 13232 (2010)

[25] Lutfor MR, Yusoff MM, Hegde G, Fazli MN, Malik A, Samah NA, Mol. Cryst. Liq. Cryst., 13, 587, 4 (2013)

[26] Rahman ML, Kumar S, Tschierske C, Israel G, Ster D, Gurumurthy H, Liq. Cryst., 36, 397 (2009)

[27] Rahman ML, Gurumurthy H, Azazpour M, Yusoff MM, Kumar S, J. Fluor. Chem., 156, 230 (2013)

[28] Barbero G, Evangelista LR, Komitov L, Phy. Rev. E., 65, 041719 (2002)