聚(杯芳烃-哌嗪)酰胺与2,2'-联吡啶超分子泡沫网络结构的构筑

doi:10.7503/cjcu20180131

高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (10): 2327.doi: 10.7503/cjcu20180131

聚(杯芳烃-哌嗪)酰胺与2,2'-联吡啶超分子泡沫网络结构的构筑

苗瑞祥^1,³, 刘冬青¹(), 任顺¹, 朱泽晛¹, 陈英波¹, 张宇峰²

1. 天津工业大学材料科学与工程学院, 省部共建分离膜与膜过程国家重点实验室, 天津 300387
2. 天津城建大学环境与市政工程学院, 天津 300384
3. 山东一诺威聚氨酯股份有限公司, 淄博 255086

收稿日期:2018-02-12 出版日期:2018-09-29 发布日期:2018-09-29
作者简介:
联系人简介: 刘冬青, 女, 博士, 副教授, 主要从事功能高分子材料研究. E-mail: ldqnov@163.com
基金资助:
国家自然科学基金(批准号: 51373119, E030701)资助.

Foams of Supramolecular Network Constructed by Poly(calixarene-piperazine) Amide and 2,2'-Bipyridine^†

MIAO Ruixiang^1,³, LIU Dongqing^1,^*(), REN Shun¹, ZHU Zexian¹, CHEN Yingbo¹, ZHANG Yufeng²

1. School of Material Science and Engineering, State Key Laboratory of Separation Membranes and Membrane Processes, Tianjin Polytechnic University, Tianjin 300387, China
2. School of Environmental and Municipal Engineering, Tianjin Chengjian University, Tianjin 300384, China
3. Shandong INOV Polyurethane Co., Ltd., Zibo 255086, China

Received:2018-02-12 Online:2018-09-29 Published:2018-09-29
Contact: LIU Dongqing E-mail:ldqnov@163.com
Supported by:
† Supported by the National Nature Science Foundation of China(Nos.51373119, E030701).

摘要/Abstract

摘要：

大环番衍生物单体5,11,17,23-四叔丁基-25,27-二酰氯基-26,28-二羟基杯[4]芳烃(DC)与哌嗪通过界面聚合, 制备了聚(杯芳烃-哌嗪)酰胺(D). 化合物D在乙酸乙酯溶液中形成平均直径为28和164 nm的双分布囊泡形聚集体. 2,2'-联吡啶(bpy)对化合物D的交联作用可将囊泡转变为实心无规则交联网. 水将交联网转变为两相界面处存在的泡沫. 这个变化过程表明, 化合物D在不同的诱导条件下可调整聚集状态, 多重诱因使其最终形成宏观泡沫状自组装构筑. 化合物D是一个集合芳香大环-小杂环, 疏水-亲水、氢键供体受体、刚性-柔性及富π空腔等多种结构及自组装于一体的高分子结构, 其分子链在不同诱因下改变扭曲和取向导致超分子交联网络的形成. 这种可逆宏观自组装现象为自组装机理的理解及刺激-响应材料的开发提供了一种有价值的试材.

关键词: 诱导自组装, 聚(杯芳烃-哌嗪)酰胺, 2,2'-联吡啶, 超分子交联网络

Abstract:

Calixarene derivative, 5,11,17,23-tetra-tert-butyl-25,27-di(chloroacetyloxy)-26,28-dihydroxycalix[4]arene(DC), was used as organic phase monomer to prepare poly(calixarene-piperazine)amide(D) through interfacial polymerization with piperazine aqueous solution. Compound D showed induced self-assembly actions under different factors. It could self-associate into double distribution vesicles of average diameter of 28 and 164 nm, respectively. 2,2'-bipyridine(bpy) crosslinked D into supermolecular network. H₂O turned network into foams at the interface of water-ethyl acetate. Foams are large-scale structure constructed by D and bpy and H₂O droven by weak intermolecular interaction including π-π staking, hydrophobic-hydrophobic interaction and interfacial effect. This work provide a new material for large scale supermolecular building and stimuli-responsive function.

Key words: Induced self-assembly, Poly(calixarene-piperazine)amide, 2,2'-Bipyridine, Supermolecular network

中图分类号:

O631.4

TrendMD:

苗瑞祥, 刘冬青, 任顺, 朱泽晛, 陈英波, 张宇峰. 聚(杯芳烃-哌嗪)酰胺与2,2'-联吡啶超分子泡沫网络结构的构筑. 高等学校化学学报, 2018, 39(10): 2327.

MIAO Ruixiang,LIU Dongqing,REN Shun,ZHU Zexian,CHEN Yingbo,ZHANG Yufeng. Foams of Supramolecular Network Constructed by Poly(calixarene-piperazine) Amide and 2,2'-Bipyridine^†. Chem. J. Chinese Universities, 2018, 39(10): 2327.

图/表 9

Table 1 GPC data of compound D

Sample	M_n	M_w	M_z	M_w/M_n
D_NS	11994	14708	17770	1.226
D_S	136762	5.60×e³⁴	—	—

Fig.1 FTIR(A), 1H NMR(B) spectra and TG(C) and DSC(D) curves of DNS

Fig.2 Tyndall effect(A), PDI-concentration curve(B), DLS curve(C), Abs-λ curves(D) and Abs-concentration curve(E) of self-assembly of compound D in ethyl acetateConcentration of DNS/(μmol·L-1): a. 2.21; b. 11; c. 55.4; d. 110.8; e. 227; f. 554; g. 831; h. 1108; i. 1385; j. 1663; k. 2210; l. 2480.

Fig.3 TEM image(A) and different magnification high resolution TEM images[(B) and (C)] of 2210 μmol/L DNS in ethyl acetate solution

Scheme 1 Self-assembly of compound D of different configuaration of calix[4]arene(A) D with calix[4]arene unit as cone conformation; (B) as partial cone conformation; (C) stereoscopic model of D in solution; (D) crossection of D with calix[4]arene unit as cone conformation; (E) crossection of D with calix[4]arene unit as of partial cone conformation; (F) aggregates crossection of D of cone calix[4]arene; (G) aggregates crossection of D of partial cone calix[4]arene.

Fig.4 Fluorescence curves of different n(bpy)/n[(D+bpy](A), JOB’s plot in fluorescence curve(B), Abs-λ curves of different amount of bpy(C) and absorbance at 295 nm in Abs-λ curve(D)(A)n(bpy)/n[(D+bpy)]: a. 0; b. 0.05; c. 0.1; d. 0.15; e. 0.2; f. 0.25; g. 0.275; h. 0.3; i. 0.325; j. 0.35; k. 0.375; l. 0.4; m. 0.425; n. 0.45; o. 0.475; p. 0.5; q. 0.55; r. 0.6; s. 0.65; t. 0.7; u. 0.75; v. 0.8; w. 0.85; x. 0.9; y. 0.95; z. 1.

Fig.5 TEM images of 1.1 mmol/L D EtOAc sotution with different amount of bpy(A—D), photo(E) and TEM image(F) of foams at intersurface between D EtOAc solution and bpy aqueous solutionn(bpy)/n(D): (A) 0; (B) 0.1; (C) 0.67; (D) 1.

Scheme 2 Crosslink of compound D of different configuaration of calix[4] arene by bpy(A) D with calix[4]arene unit as cone conformation; (B) D with calix[4]arene unitas partial cone conformation.

Fig.6 XPS sprctra of dried foams D(A), N1s of D(B), D+bpy(C) and N1s of D+bpy(D)

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聚(杯芳烃-哌嗪)酰胺与2,2'-联吡啶超分子泡沫网络结构的构筑

Foams of Supramolecular Network Constructed by Poly(calixarene-piperazine) Amide and 2,2'-Bipyridine^†

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聚(杯芳烃-哌嗪)酰胺与2,2'-联吡啶超分子泡沫网络结构的构筑

Foams of Supramolecular Network Constructed by Poly(calixarene-piperazine) Amide and 2,2'-Bipyridine†

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Foams of Supramolecular Network Constructed by Poly(calixarene-piperazine) Amide and 2,2'-Bipyridine^†