2009
DOI: 10.1039/b911064j
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Discovery and early development of squaraine rotaxanes

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.

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Cited by 213 publications
(170 citation statements)
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References 88 publications
(56 reference statements)
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“…This effect is a result of kinetic protection against proton abstraction from the ammonium moiety by the crown ether wheel, which acts as a surrounding "bulky" group that suppresses neutralization by a base. [17] In the neutralization of ammonium salts in organic solvents, it seems most likely that neutralization occurs through initial ammonium proton abstraction by a basic nucleophile present in the system, but not through direct dissociation to a proton and free amine, especially in the present system.…”
Section: Resultsmentioning
confidence: 97%
“…This effect is a result of kinetic protection against proton abstraction from the ammonium moiety by the crown ether wheel, which acts as a surrounding "bulky" group that suppresses neutralization by a base. [17] In the neutralization of ammonium salts in organic solvents, it seems most likely that neutralization occurs through initial ammonium proton abstraction by a basic nucleophile present in the system, but not through direct dissociation to a proton and free amine, especially in the present system.…”
Section: Resultsmentioning
confidence: 97%
“…[6] Thus, intensive efforts have been directed toward the development of turn-on fluorescent sensors, which have become mainstream. [7] Among various strategies, the chemodosimeter approach [8] provides good opportunities to design turn-on sensors for transition-metal ions with both high sensitivity and selectivity.…”
Section: Introductionmentioning
confidence: 99%
“…Additionally reported in the first Treibs and Jacob paper was a note that the pyrrolyl squaraines under investigation discoloured in solutions of amines in ethanol [1]. This was the first observation that squaraine dyes are susceptible to attack by strong nucleophiles, with a solution to this problem taking almost 40 years to be reported; in 2004 with the preparation of squaraine rotaxanes [85].…”
Section: The Beginning: the First Three Yearsmentioning
confidence: 99%