方酸轮烷的发现与早期发展。
Discovery and early development of squaraine rotaxanes.
机构信息
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
出版信息
Chem Commun (Camb). 2009 Nov 14(42):6329-38. doi: 10.1039/b911064j. Epub 2009 Aug 24.
Abstract
The chemical and photophysical properties of a fluorescent squaraine dye are greatly enhanced when it is mechanically encapsulated inside a tetralactam macrocycle. This feature article describes the synthesis, structure, and photophysical performance of first-generation squaraine rotaxanes, and shows how they can be used as fluorescent imaging probes and chemosensors.
摘要
当荧光方酸染料被机械包裹在四元内酰胺大环内时，其化学和光物理性质会得到极大增强。本文介绍了第一代方酸轮烷的合成、结构和光物理性能，并展示了它们如何用作荧光成像探针和化学传感器。
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本文引用的文献
1
High-Yielding Rotaxane Synthesis with an Anion Template.
Angew Chem Int Ed Engl. 1999 Feb 1;38(3):383-386. doi: 10.1002/(SICI)1521-3773(19990201)38:3<383::AID-ANIE383>3.0.CO;2-H.
2
Singlet oxygen generation using iodinated squaraine and squaraine-rotaxane dyes.
New J Chem. 2007 Jan 1;31(5):677-683. doi: 10.1039/b616224j.
3
Effect of Stopper Size on Squaraine Rotaxane Stability.
Supramol Chem. 2009 Jan;21(1-2):118-124. doi: 10.1080/10610270802468454.
4
Cycloaddition to an anthracene-derived macrocyclic receptor with supramolecular control of regioselectivity.
Chem Commun (Camb). 2009 May 14(18):2517-9. doi: 10.1039/b901814j. Epub 2009 Mar 23.
5
Water-soluble BODIPY derivatives.
Org Lett. 2009 May 21;11(10):2049-52. doi: 10.1021/ol900302n.
6
Polyfluorophores on a DNA backbone: a multicolor set of labels excited at one wavelength.
J Am Chem Soc. 2009 Mar 25;131(11):3923-33. doi: 10.1021/ja805502k.
7
Spectral properties of self-assembled squaraine-tetralactam: a theoretical assessment.
Phys Chem Chem Phys. 2009 Feb 28;11(8):1258-62. doi: 10.1039/b817720a. Epub 2009 Jan 12.
8
Bright, color-tunable fluorescent dyes in the Vis/NIR region: establishment of new "tailor-made" multicolor fluorophores based on borondipyrromethene.
Chemistry. 2009;15(5):1096-106. doi: 10.1002/chem.200801906.
9
Green fluorescent protein glows gold.
Cell. 2008 Dec 12;135(6):987-90. doi: 10.1016/j.cell.2008.11.025.
10
The green fluorescent protein: a key tool to study chemical processes in living cells.
Angew Chem Int Ed Engl. 2008;47(47):8992-4. doi: 10.1002/anie.200804998.
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