Synthesis and Characterization of Novel Troger’s Base Containing Polymers from Commercial Available Diamines

Zhixiu Wu; Jianyong Jin

Macromolecular Research, Vol.25, No.6, 546-551, June, 2017

DOI10.1007/s13233-017-5131-8 Export Citation

Synthesis and Characterization of Novel Troger’s Base Containing Polymers from Commercial Available Diamines

Zhixiu Wu, and Jianyong Jin^†

School of Chemical Sciences, Private Bag 92019, University of Auckland, 23 Symonds St, Auckland 1142, New Zealand

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For potential use as multifunctional nitrogen containing polymers in catalysts, antimicrobial and microporous materials, three novel step growth polymers containing Troger’s base (TBPs) were designed and synthesized by typical Troger’s Base condensation using cheap commercial available aromatic diamine sources including 4,4'- diaminodiphenylmethane (MDA), 4,4'-diaminodiphenyl ether (4,4’- ODA), and 4,4'- (hexafluoroisopropylidene)dianiline (BisAAF). FT-IR, 1H NMR, and GPC analysis were employed to obtain the compositional and structural information. Both TBP-1 and TBP-2 were insoluble in most common organic solvents whereas TBP-3, haloalkanes, held more promising solubility. The number average molecular weights (Mn) of all three TBPs were close to 30,000 g/mol. Thermal properties were gained from TGA and DSC measurements. TBP-1 and TBP-3 were relatively more thermal stable than TBP-2 while their overall Td (5%) were less than 200°C. The glass transition temperatures for all three TBPs were not observed between room temperature and their thermal decomposition. Protonation of TBP-1 was attempted and revealed the instability of quaternized Troger’s base structures.

Keywords:Troger’s base;step growth polymerization;quaternization;microporous polymer

[References]

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[1] Troger J, J. Prakt. Chem., 36, 225 (1887)

[2] Spielman MA, J. Am. Chem. Soc., 57, 583 (1935)

[3] Runarsson OV, Artacho J, Warnmark K, Eur. J. Org. Chem., 2012(36), 7015 (2012)

[4] Wu H, Chen XM, Wan Y, Ye L, Xin HQ, Xu HH, Yue CH, Pang LL, Ma R, Shi DQ, Tetrahedron Lett., 50, 1062 (2009)

[5] Webb TH, Wilcox CS, Chem. Soc. Rev., 22, 383 (1993)

[6] Johnson RA, Gorman RR, Wnuk RJ, Crittenden NJ, Aiken JW, J. Med. Chem., 36, 3202 (1993)

[7] Demeunynck M, Tatibouet A, Prog. Heterocycl. Chem., 11, 1 (1999)

[8] Abdolmaleki A, Heshmat-Azad S, Kheradmand-fard M, J. Appl. Polym. Sci., 122(1), 282 (2011)

[9] Du X, Sun Y, Tan B, Teng Q, Yao X, Su C, Wang W, Chem. Commun., 46, 970 (2010)

[10] Jeon YM, Armatas GS, Kim D, Kanatzidis MG, Mirkin CA, Small, 5, 46 (2009)

[11] Carta M, Malpass-Evans R, Croad M, Rogan Y, Jansen JC, Bernardo P, Bazzarelli F, McKeown NB, Science, 339(6117), 303 (2013)

[12] Carta M, Croad M, Malpass-Evans R, Jansen JC, Bernardo P, Clarizia G, Friess K, Lanc M, McKeown NB, Adv. Mater., 26(21), 3526 (2014)

[13] Zhu X, Do-Thanh CL, Murdock CR, Nelson KM, Tian C, Brown S, Mahurin SM, Jenkins DM, Hu J, Zhao B, ACS Macro Lett., 2, 660 (2013)

[14] Didier D, Tylleman B, Lambert N, Vande Velde CML, Blockhuys F, Collas A, Sergeyev S, Tetrahedron, 64, 6252 (2008)

[15] Hansson A, Jensen J, Wendt OF, Warnmark K, Eur. J. Org. Chem., 2003, 3179 (2003)

[16] Bhuiyan MDH, Mahon AB, Jensen P, Clegg JK, Try AC, Eur. J. Org. Chem., 2009, 687 (2009)

[17] Becker DP, Finnegan PM, Collins PW, Tetrahedron Lett., 34, 1889 (1993)

[18] Carta M, Malpass-Evans R, Croad M, Rogan Y, Lee M, Rose I, McKeown NB, Polym. Chem., 5, 5267 (2014)

[19] Socrates G, Infrared Characteristic Group Frequencies, Wiley-Interscience, Chichester, 1980.

[20] Revesz A, Schroder D, Rokob TA, Havlik M, Dolensky B, Angew. Chem.-Int. Edit., 50, 2401 (2011)