Gassensmith Jeremiah J, Barr Lorna, Baumes Jeffrey M, Paek Agelina, Nguyen Anh, Smith Bradley D
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Org Lett. 2008 Aug 7;10(15):3343-6. doi: 10.1021/ol801189a. Epub 2008 Jun 27.
Pseudorotaxane complexes of squaraine dyes and tetralactam macrocycles are converted into permanently interlocked rotaxane structures using copper-catalyzed and copper-free cycloaddition reactions with bulky stopper groups. The photophysical properties of the encapsulated squaraine depend on the structure of the macrocycle. In one case, squaraine rotaxanes are produced in near-quantitative yields and with intense near-IR fluorescence. In another case, squaraine fluorescence is greatly diminished upon macrocyclic encapsulation but the signal can be restored by dye displacement with anions.
方酸菁染料与四内酰胺大环的准轮烷配合物通过与庞大的封端基团进行铜催化和无铜环加成反应,转化为永久互锁的轮烷结构。被包封方酸菁的光物理性质取决于大环的结构。在一种情况下,方酸菁轮烷以近定量的产率生成,并具有强烈的近红外荧光。在另一种情况下,大环包封后方酸菁荧光大大减弱,但通过用阴离子置换染料可恢复信号。