New poly(bismaleimide‐diamine)s containing crown‐ether groups in the main chain

Abstract

A series of new poly(bisma1eimide-diamine)s (3 ac) with crown-ether groups in the main chain were synthesized from bismaleimides (1 a-c) and a diamino-functional dibenzo-18-crown-6 (2). The polymerization occurred in solution through the addition of the NH, groups of 2 to the C = C double bonds of the maleimide rings of 1. The optimum polymerization conditions were established. The polymers 3 were obtained in good yields and fairly high molecular weights (qred = 0,15-0,35 dL/g). The polymeric crown ethers show high capacity for the binding of alkali metal ions and may be used as selective sorbents.

Polyamide Pseudorotaxanes, Rotaxanes, and Catenanes Based on Bis(5-carboxy-1,3-phenylene)-(3x+2)-crown-x Ethers

“…The cluster at m/z ∼ 2866 Da (Figure 9b) corresponds to the silver adduct of the macrocyclic tetramer (M 4 ) that has lost CO 2 : 4(700.27) -44 + 106.95 ) 2864 and 4(700.27) -44 + 108.95 ) 2866 for 107 Ag (51.3%) and 109 Ag (48.7%), respectively. The remaining signals for the predominant cyclic species are observed as (M + H) + , (M + Na) + and (M + K) + adducts, as illustrated for the tetramers M 4 (exact mass 2801.06 for 12 C 152 1 H 160 14 N 8 16 O 44 ) in the series of signals at m/z ) 2800-2840 (Figure 9c); the corresponding silver adducts (M 4 + Ag) + (theory: 2908 and 2910) are observed in Figure 9b in the cluster at m/z ∼ 2911 Da.…”

“…Here linear structures that would exhibit signals at m/z ) 992n + 18 (AA), 992n + 536 (DAc), and 992n + 200 (DAm) are completely absent. Figure 10b is an expanded view of the series of signals from 2970 to 3030, corresponding to the cyclic trimers (exact mass 2977.01, 12 C 168 1 H 159 14 N 6 16 O 39 31 P 3 ) containing (M 3 + H) + , (M 3 + Na) + and (M 3 + K) + clusters.…”

“…Crown ethers are an important class of compounds that undergo complexation with metal ions and other species, in some cases leading to the formation of threaded structures known as pseudorotaxanes and rotaxanes . Polymers containing small crown ethers, most commonly 18-membered rings, were known as early as 1970, mainly for study of cation binding. − Polyaramides derived from dibenzo-18-crown-6 have been made via interfacial polymerization of diaminodibenzo-18-crown-6 with aromatic and aliphatic diacid chlorides. − A variety of other approaches has produced polymers containing crown ethers. − …”

“…[5][6][7] A variety of other approaches has produced polymers containing crown ethers. [8][9][10][11][12][13][14] In our laboratory, we have utilized crown ethers to synthesize a variety of polypseudorotaxanes and polyrotaxanes (Scheme 1). 2,[15][16][17][18][19][20][21][22][23][24][25][26] By carrying out step-growth polymerizations in the presence of crown ethers, main chain polypseudorotaxanes of type A (Scheme 1) were prepared based on polyester 15,16 and polyurethane backbones.…”

Crown ethers in radiochemistry. Advances and prospects

“…Kurmanaliev et al 32 described synthesis of polyimides 10a,b containing the structural moiety of diaminodicyclohexano-18-crown-6 or diaminodicyclohexano-24-crown-8 and studied the transport of alkali metal cations through thin films of these polymers (Scheme 3). For polymer 10a, the selectivity of the cation transport changes in the order K + > Cs + > Na + and for polymer 10b it changes in the order Cs + > K + > Na + .…”