Optically active poly(amide-imide)s containing axially dissymmetric 1,1?-binaphthyl moieties

Abstract

Novel optically active aromatic poly(amide–imide)s (PAIs) were prepared from newly synthesized 2,2′‐bis(3,4‐dicarboxybenzamido)‐1,1′‐binaphthyl dianhydride ((+)‐, (S)‐, and (R)‐BNDADA). PAIs based on dianhydride monomers with different ee % were investigated with respect to their structures and chiroptical properties. These polymers were highly soluble in polar aprotic solvents such as N,N‐dimethylacetamide, N‐methyl‐2‐pyrrolidone, pyridine, etc., and showed high glass transition temperatures of 287–290°C and 5% weight loss temperatures of 450–465°C in nitrogen. Optically active PAIs exhibited high specific rotations, excellent optical stabilities, and a dependence of optical activities on temperature. Investigations on chiroptical properties indicated that chiral conformation was possessed by optically active PAIs. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3147–3154, 1999

Synthesis and chirooptical properties of optically active poly(ester imide)s based on axially asymmetric 1,1′‐binaphthyls

“…Solubility tests showed better solubility for the resulting PEsI's than for previously synthesized poly(ether imide)s and poly(amide imide)s 10, 11. All the PEsI's were readily soluble in both polar aprotic solvents (DMAc and DMSO) and less polar solvents (e.g., THF and chloroform), except for the polymers based on 1,4‐phenylene diamine, which were partially soluble in chloroform (Table 2).…”

“…Main‐chain helical19 and second‐order NLO polymers based on chiral 1,1‐binaphthyls20 have also been reported, the researchers taking advantage of their strong ability to impose an asymmetric environment in the proximity. In our early studies,10, 11 1,1′‐binaphthyl‐based chiral bis(ether anhydride)s (BEDAs) and bis(amide anhydride)s (BNDADAs; Fig. 1) were synthesized and used to produce optically active poly(ether imide)s and poly(amide imide)s, respectively.…”

Advances in synthetic optically active condensation polymers - A review

“…These PAIs exhibited excellent solubility in the organic solvents at room temperature. Song et al [189] prepared newly optically active aromatic PAIs from polycondensation reaction of 2,2!-bis(3,4-dicarboxybenzamido)-1,1!-binaphthyl dianhydride and different diamines in DMAc (Figure 17). Polymers with different ee% were investigated with respect to their structures and chiroptical properties.…”

“…Poly(ester-amide)s (PEA)s are emerging as promising materials for a wide range of biomedical applications due to their potential for both hydrolytic and [189] enzymatic degradation as well as the ease with which their properties can be tuned by the choice of monomers. The architecture of the PEA polymers is a blend of PA and PE polymer character.…”

Synthesis and characterization of fluorinated polyimides derived from novel unsymmetrical diamines

“…Thus, many studies have focused on designing such chemical structures of the rigid aromatic backbone so as to obtain aromatic polymers that are processable by conventional techniques, while maintaining desirable properties. For example, bulky lateral substituents [3][4][5], flexible linkages [6][7][8], noncoplanar biphenyl moieties [9,10] as well as unsymmetrical structures [11][12][13] have been used to enhance the solubility of aromatic polymers make them processability.…”