A pillar[5]arene-based three-component supramolecular copolymer for the fluorescence detection of spermine†

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-09-18 DOI:10.1039/D4QO01470G

Martina Mazzaferro, Daniele Crisafulli, Francesca Mancuso, Marco Milone, Fausto Puntoriero, Anna Irto, Salvatore Patanè, Valentina Greco, Alessandro Giuffrida, Ilenia Pisagatti, Anna Notti, Melchiorre F. Parisi and Giuseppe Gattuso

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Abstract

The supramolecular polymerization of a bis-pillar[5]arene dicarboxylic acid monomer (H) in the presence of a mixture of complementary bis-guests 1,12-dodecanediyl-bis-1,1′-1H-imidazole (G1) and bis-N,N’-(6-(1H-imidazole)decyl)-perylene bisimide (G2), produces an AA/BB-type supramolecular copolymer H/G1/G2 that retains the properties of the parent bi-component systems, that is, H/G1 solubility and H/G2 photoresponsiveness. The supramolecular copolymer showed stimuli-responsiveness, reacting to the presence of the cancer marker, spermine (S), by disassemblying and releasing G2. Once released, the perylene bisimide monomer (quenched in the copolymer by host-to-guest electron transfer), showed a remarkable increase of emission intensity. ESI-MS data are fully consistent with the formation of the H/G1/G2 copolymer, and AFM investigations on films cast from H/G1/G2 and H/G1/G2 + S solutions demonstrated that the supramolecular copolymer sensing abilities are retained also in the solid state.

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用于荧光检测精胺的柱[5]炔基三组份超分子共聚物

双柱[5]炔二羧酸单体（H）在互补双试剂-1,12-十二烷二基-双-1,1′-1H-咪唑（G1）和双-N、N'-(6-(1H-咪唑)癸基)-亚珀双亚胺(G2)-的混合物产生了 AA/BB 型超分子共聚物 H/G1/G2，它保留了母体双组分系统的特性，即 H/G1 的溶解性和 H/G2 的光响应性。这种超分子共聚物具有刺激响应性，在癌症标记物精胺（S）存在时会发生反应，分解并释放出 G2。一旦释放出来，过二亚胺单体（通过主客体间的电子转移在共聚物中淬灭）的发射强度显著增加。ESI-MS数据与H/G1/G2共聚物的形成完全一致，对H/G1/G2和H/G1/G2 + S溶液浇铸的薄膜进行的原子力显微镜研究表明，超分子共聚物的传感能力在固态下也得以保留。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.