Chemoselective Polycondensation of 2-Amino-4,6-dichloro-1,3,5-triazine with Aromatic Diamines

Abstract

Chemoselective polycondensation of 2-amino-4,6-dichloro-1,3,5-triazine (ADCT) was investigated with various aromatic diamines such as 4,4′-oxydianiline (ODA), 9,9-bis(4-aminophenyl)fluorene (BAFL), 4,4′-(hexafluoropropane-2,2-diyl)dianiline (BisAF), and bis(4-aminophenyl)sulfone (SODA) in the presence of potassium carbonate as a base. High-molecular weight perfectly linear polyguanamines (Mn ≈ 46000) were successfully obtained for the polycondensation of ADCT with BisAF, while the polycondensation of ADCT with BAFL afforded branched polyguanamines with a degree of branching of from 0.02 to 0.17.

Synthesis of highly refractive and highly fluorescent rigid cyanuryl polyimines with polycyclic aromatic hydrocarbon pendants

“…In our previous work, the T g values of poly(ADCT-BAFL) and poly(BDCT-BAFL) were determined to be 266 °C and 237 °C, respectively, 17,18 suggesting that the introduction of a PAH unit more effectively suppresses the chain movement in the polymeric structure than an amino group (NH 2 ) does on the ADCT unit. The high thermostability was confirmed by the 5 wt%-loss temperature (T d5 ) above 352 °C, which is attributable to completely aromatic polymeric structures.…”

“…[10][11][12][13][14][15][16] We previously reported the chemoselective polycondensation of 2-amino-4,6-dichlorotriazine (ADCT) with 4,4′-(9-fluorenylidene)dianiline (BAFL), where the amino functional group on the ADCT monomer was nearly inert during polymerization, in a chemoselective manner. 17 However, BAFL was the only effective diamine monomer to afford a high molecular weight soluble polymer (number average molecular weight: M n = 19 000). We speculated the existence of a multiple-hydrogen interaction between poly-meric chains.…”

“…[28][29][30][31] In our previous work, ADCT with BAFL was only the case to afford a high molecular weight soluble polymer. 17 Fig. 1 shows the 1 H and 13 C NMR spectra of poly(αDCNT-pPDA) in DMSO-d 6 at 20 °C.…”

Fine structural analysis, formation of interfacial particle films, and accurate estimation of orientation in polyguanamine derivatives with a high refractive index

“…If there are simultaneously dense amorphous regions and a very tight molecular chain packing, it may be possible to produce new polymeric materials having a high refractive index. In recent years, preliminary data on the attainment of a refractive index of 1.9 in polyguanamine derivatives have been reported . Judging from its molecular structure, it is unlikely that the physical properties are enhanced only by introduction of the functional group species.…”

Excellent performance of aromatic polyguanamines induced by multiple hydrogen bondable tetraazacalix[2]arene[2]-triazine ring in their main chain

“…They are usually prepared from triazine dichloride and diamine monomers in solution, with a variety of derivatives having been synthesized to date. [27][28][29][30][31][32][33][34] The guanamine functional group was also found in Wang's aza-bridged calix [2] arene [2]triazine (mPDA 2 CyC 2 ), which has two active C-Cl bonds; therefore, we expected that a mPDA 2 CyC 2 residue would exhibit a unique effect on PG structure. In particular, if rigid aromatic diamines were combined with mPDA 2 CyC 2 during polycondensation, then a new series of condensation polymers having a tightly packed structure should be obtained.…”