环状供体-受体电路：一种混合杂环脱氢轮烯型环番的合成及荧光离子传感特性

Cyclic donor-acceptor circuits: synthesis and fluorescence ion sensory properties of a mixed-heterocyclic dehydroannulene-type cyclophane.

作者信息

Baxter Paul N W

机构信息

Institut Charles Sadron, UPR 022, 6 Rue Boussingault, F-67083 Strasbourg, France.

出版信息

J Org Chem. 2004 Mar 19;69(6):1813-21. doi: 10.1021/jo0302410.

DOI:10.1021/jo0302410

PMID:15058923

Abstract

The new dehydroannulene-type cyclophane 5 comprising a conjugated helical framework of thiophene (electron donor) and pyridine (electron acceptor) heterocyclic units has been prepared. Macrocycle 5 was characterized by FAB MS and (1)H and (13)C NMR spectroscopy. Cycle 5 was found to function as a selective precipitation and fluorescence sensor for specific metal ions such as Ag(I) and also exhibited reversible proton-triggered fluorescence quenching behavior. The unique donor-acceptor architecture and spectroscopic properties of 5 suggest that it represents a novel lead class of molecular sensory platforms, with many potential future applications in 21st century materials science.

摘要

新型脱氢轮烯型环番5已被制备出来，它包含噻吩（电子供体）和吡啶（电子受体）杂环单元的共轭螺旋骨架。大环化合物5通过快原子轰击质谱（FAB MS）以及氢核磁共振（¹H NMR）和碳核磁共振（¹³C NMR）光谱进行了表征。发现环番5可作为特定金属离子（如Ag(I)）的选择性沉淀和荧光传感器，并且还表现出可逆的质子触发荧光猝灭行为。5独特的供体-受体结构和光谱性质表明，它代表了一类新型的分子传感平台先导物，在21世纪材料科学中有许多潜在的未来应用。