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
{"title":"用于荧光检测精胺的柱[5]炔基三组份超分子共聚物","authors":"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","doi":"10.1039/D4QO01470G","DOIUrl":null,"url":null,"abstract":"<p >The supramolecular polymerization of a bis-pillar[5]arene dicarboxylic acid monomer (<strong>H</strong>) in the presence of a mixture of complementary bis-guests 1,12-dodecanediyl-bis-1,1′-1<em>H</em>-imidazole (<strong>G1</strong>) and bis-<em>N</em>,<em>N’</em>-(6-(1<em>H</em>-imidazole)decyl)-perylene bisimide (<strong>G2</strong>), produces an AA/BB-type supramolecular copolymer <strong>H</strong>/<strong>G1</strong>/<strong>G2</strong> that retains the properties of the parent bi-component systems, that is, <strong>H</strong>/<strong>G1</strong> solubility and <strong>H</strong>/<strong>G2</strong> photoresponsiveness. The supramolecular copolymer showed stimuli-responsiveness, reacting to the presence of the cancer marker, spermine (<strong>S</strong>), by disassemblying and releasing <strong>G2</strong>. 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 <strong>H</strong>/<strong>G1</strong>/<strong>G2</strong> copolymer, and AFM investigations on films cast from <strong>H</strong>/<strong>G1</strong>/<strong>G2</strong> and <strong>H</strong>/<strong>G1</strong>/<strong>G2</strong> + <strong>S</strong> solutions demonstrated that the supramolecular copolymer sensing abilities are retained also in the solid state.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/qo/d4qo01470g?page=search","citationCount":"0","resultStr":"{\"title\":\"A pillar[5]arene-based three-component supramolecular copolymer for the fluorescence detection of spermine†\",\"authors\":\"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\",\"doi\":\"10.1039/D4QO01470G\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >The supramolecular polymerization of a bis-pillar[5]arene dicarboxylic acid monomer (<strong>H</strong>) in the presence of a mixture of complementary bis-guests 1,12-dodecanediyl-bis-1,1′-1<em>H</em>-imidazole (<strong>G1</strong>) and bis-<em>N</em>,<em>N’</em>-(6-(1<em>H</em>-imidazole)decyl)-perylene bisimide (<strong>G2</strong>), produces an AA/BB-type supramolecular copolymer <strong>H</strong>/<strong>G1</strong>/<strong>G2</strong> that retains the properties of the parent bi-component systems, that is, <strong>H</strong>/<strong>G1</strong> solubility and <strong>H</strong>/<strong>G2</strong> photoresponsiveness. The supramolecular copolymer showed stimuli-responsiveness, reacting to the presence of the cancer marker, spermine (<strong>S</strong>), by disassemblying and releasing <strong>G2</strong>. 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A pillar[5]arene-based three-component supramolecular copolymer for the fluorescence detection of spermine†
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.
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.
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