Synthesis and Characterization of Noncentrosymmetric Main Chain Hydrogen Bonded Macromolecules Incorporating an Azo-Stilbazole Acceptor

Daniel J. Dyer; Jeremy R. Wolf

Macromolecular Research, Vol.22, No.8, 870-874, August, 2014

DOI10.1007/s13233-014-2105-y Export Citation

Synthesis and Characterization of Noncentrosymmetric Main Chain Hydrogen Bonded Macromolecules Incorporating an Azo-Stilbazole Acceptor

Daniel J. Dyer¹, and Jeremy R. Wolf^{1, 2, †}

¹Department of Chemistry, Southern Illinois University Carbondale, 1245 Lincoln Drive, Carbondale, IL, 62901, USA
²ABC Laboratories, 7200 E. ABC Lane, Columbia, MO, 65202, USA

E-mail:

The syntheses and characterization of three noncentrosymmetric main chain hydrogen bonded macromolecules which incorporate diethyl-[4-(pyridin-4-ylazo)-phenyl]-amine hydrogen bond acceptor units are reported. These macromolecules participate in strong intermolecular hydrogen bonding as demonstrated using attenuated total reflectance (ATR) FTIR. The phase transitions of these macromolecules depend on the identity of the hydrogen bond donor. Mixtures of these azo-stilbazole macromolecules with noncentrosymmetric hydrogen bonded liquid crystalline macromolecules possess nematic liquid crystalline phases when the concentration of the azo-stilbazole macromolecule is ≤ 50 mol%.

Keywords:hydrogen bonded macromolecules;azo-stilbazole.

[References]

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Polarizabilities calculated using Hyperchem 7.0. Geometries were optimized at the PM3 level using termination conditions of RMS gradient=0.01 kcal/mol.
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Lam LKT, Yee C, Pai RP, Wattenberg LW, Org. Prep. Proc., Int., 14, 241 (1982)
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Dyer DJ, Li C, Wolf J, Landorf C, Zhao T, Polymer Prepr., 44, 713 (2003)
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Xu JW, Toh CL, Liu XM, Wang SF, He CB, Lu XH, Macromolecules, 38(5), 1684 (2005)
Kato T, Frechet JMJ, Macromol. Symp., 98, 311 (1995)
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[2] Butcher PN, Cotter D, The Elements of Nonlinear Optics, Cambridge University, New York (1990)

[3] Skobel’tsyn DV, Nonlinear Optics, Consultants Bureau, New York (1970)

[4] Baldwin GC, An Introduction to Nonlinear Optics, Plenum, New York (1969)

[5] Schwodiauer R, Neugschwandtner GS, Schrattbauer K, Lindner M, Vieytes M, Bauer-Gogonea S, Bauer S, IEEE Trans. Dielectr. Electr. Insul., 7, 578 (2000)

[6] Petty MC, Meas. Sci. Technol., 7, 725 (1996)

[7] Tsibouklis J, Petty M, Petty MC, Feast WJ, Int. J. Electron., 78, 1101 (1995)

[8] Eberle G, Schmidt H, Eisenmenger W, IEEE Trans. Dielectr. Electr. Insul., 3, 624 (1996)

[9] Chen QX, Payne PA, Meas. Sci. Technol., 6, 249 (1995)

[10] Varanasi PR, Jen AK, Chandrasekhar J, Namboothiri IN, Rathna A, J. Am. Chem. Soc., 118(49), 12443 (1996)

[11] Yu ZH, Li LT, Fu W, Li LP, J. Phys. Chem. A, 102(11), 2016 (1998)

[12] Brown CJ, Acta Crystallogr., 21, 146 (1966)

[13] Robertson JM, J. Chem. Soc., 232 (1939)

[14] Robertson J, Prasad M, Woodwarth I, Proc. R. Soc. Lond., 154, 187 (1936)

[15] Landorf C, Wolf J, Li C, Xie W, Jacobsen J, Simpson J, Dyer DJ, Organic Thin Films for Photonic Applications. Trends in Optics and Photonics Series; Optical Society of America, 64, 145 (2002)

[16] Aoki K, Nakagawa M, Ichimura K, J. Am. Chem. Soc., 122(44), 10997 (2000)

[17] Wolf JR, Synthesis and Characterization of Noncentrosymmetric Hydrogen Bonded Liquid Crystalline Polymers, Doctoral Dissertation, Southern Illinois University (2005)

[18] Polarizabilities calculated using Hyperchem 7.0. Geometries were optimized at the PM3 level using termination conditions of RMS gradient=0.01 kcal/mol.

[19] Kovalev BG, Matveeva ED, Stan VV, Vovk GA, Yudin LG, Kost AN, Russ. J. Org. Chem., 16, 2032 (1980)

[20] Lam LKT, Yee C, Pai RP, Wattenberg LW, Org. Prep. Proc., Int., 14, 241 (1982)

[21] Brown PE, Lewis RA, Waring MA, J. Chem. Soc. Perkin 1, 11, 2979 (1990)

[22] Connoly S, Bennion C, Botterell S, Croshoaw PJ, Hallam C, Hardy K, Hartopp P, Jackson CG, King SJ, Lawrence L, Mete A, Murray D, Robinson DH, Smith GM, Stein L, Walters I, Wells E, Withnal WJl, J. Med. Chem., 45, 1348 (2002)

[23] Wissner A, Carroll ML, Green KE, Kerwar SS, Pickett WC, Schaub RE, Torley LW, Wrenn S, Kohler CA, J. Med. Chem., 35, 1650 (1992)

[24] Wolf J, Landorf C, Zhao T, Dyer DJ, Liq. Cryst., 14, 5 (2014)

[25] Lin HC, Lin YS, Liq. Cryst., 24, 315 (1998)

[26] Dyer DJ, Wolf J, Li C, Landorf C, Brown B, Maas J, Conlin E, Zhao T, Polymer Prepr, 44, 578 (2003)

[27] Dyer DJ, Li C, Wolf J, Landorf C, Zhao T, Polymer Prepr., 44, 713 (2003)

[28] Landorf C, Simpson J, Jacobsen J, Dyer DJ, Polym. Mater. Sci. Eng., 83, 172 (2000)

[29] Xu JW, Toh CL, Liu XM, Wang SF, He CB, Lu XH, Macromolecules, 38(5), 1684 (2005)

[30] Kato T, Frechet JMJ, Macromol. Symp., 98, 311 (1995)

[31] Lee YS, O’Brien DF, Chem. Phys. Lipids, 61, 209 (1992)

[32] Sonnet PE, Heath RR, J. Chem. Ecol., 6, 221 (1980)