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-烷基羧基螺吡喃的合成与金属结合特性

Synthesis and metal binding properties of -alkylcarboxyspiropyrans.

作者信息

Perry Alexis, Kousseff Christina J

机构信息

Biosciences, University of Exeter, Stocker Road, Exeter EX4 4QD, UK.

出版信息

Beilstein J Org Chem. 2017 Aug 4;13:1542-1550. doi: 10.3762/bjoc.13.154. eCollection 2017.

DOI:10.3762/bjoc.13.154
PMID:28845199
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5550821/
Abstract

Spiropyrans bearing an -alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2-12 carbon atom alkylcarboxylate substituents, and a systematic analysis of their interactions with metal cations using H NMR and UV-visible spectroscopy. All -alkylcarboxyspiropyrans in this study displayed a strong preference for binding divalent metal cations and a modest increase in M binding affinity correlated with increased alkycarboxylate tether length.

摘要

带有烷基羧酸盐连接链的螺吡喃是动态光活性材料中的常见结构，可作为比色/荧光阳离子受体。在本研究中，我们描述了一种高效合成具有2至12个碳原子的烷基羧酸盐取代基的螺吡喃的方法，并使用核磁共振氢谱和紫外可见光谱对它们与金属阳离子的相互作用进行了系统分析。本研究中的所有烷基羧基螺吡喃对二价金属阳离子的结合表现出强烈偏好，并且金属结合亲和力的适度增加与烷基羧酸盐连接链长度的增加相关。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/fc115d863ab2/Beilstein_J_Org_Chem-13-1542-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/0e656fda0675/Beilstein_J_Org_Chem-13-1542-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/420cb373bff5/Beilstein_J_Org_Chem-13-1542-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/8317efd6dbe6/Beilstein_J_Org_Chem-13-1542-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/b4fc90ff51ad/Beilstein_J_Org_Chem-13-1542-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/3a490a8bf3da/Beilstein_J_Org_Chem-13-1542-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/af04752f9908/Beilstein_J_Org_Chem-13-1542-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/1e3bfc9d3450/Beilstein_J_Org_Chem-13-1542-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/6109f25f018a/Beilstein_J_Org_Chem-13-1542-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/6d55449406c5/Beilstein_J_Org_Chem-13-1542-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/dcb860a826ff/Beilstein_J_Org_Chem-13-1542-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/fc115d863ab2/Beilstein_J_Org_Chem-13-1542-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/0e656fda0675/Beilstein_J_Org_Chem-13-1542-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/420cb373bff5/Beilstein_J_Org_Chem-13-1542-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/8317efd6dbe6/Beilstein_J_Org_Chem-13-1542-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/b4fc90ff51ad/Beilstein_J_Org_Chem-13-1542-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/3a490a8bf3da/Beilstein_J_Org_Chem-13-1542-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/af04752f9908/Beilstein_J_Org_Chem-13-1542-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/1e3bfc9d3450/Beilstein_J_Org_Chem-13-1542-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/6109f25f018a/Beilstein_J_Org_Chem-13-1542-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/6d55449406c5/Beilstein_J_Org_Chem-13-1542-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/dcb860a826ff/Beilstein_J_Org_Chem-13-1542-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf02/5550821/fc115d863ab2/Beilstein_J_Org_Chem-13-1542-g008.jpg

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本文引用的文献

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Self-assembled NIR nanovesicles for long-term photoacoustic imaging in vivo.用于体内长期光声成像的自组装近红外纳米囊泡。
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