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Issue 78, 2017
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Fluorogenic NIR-probes based on 1,2,4,5-tetrazine substituted BF2-azadipyrromethenes

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Abstract

A series of 1,2,4,5-tetrazine integrated near infrared (NIR) fluorophores based on the BF2 azadipyrromethene (NIR-AZA) class has been synthesised and their ability to modulate emission from low to high in response to Diels–Alder cycloaditions has been assessed. Substituents on the tetrazine component of the probe (Cl, OMe, p-NO2C6H4O) were seen to strongly influence quantum yields, fluorescence enhancement factors, and rates of cycloadditions. Cycloadditions between tetrazine-NIR-AZA constructs and a strained alkyne substrate were seen to be highly efficient in organic or aqueous solutions and in gels with high fluorescence enhancements of up to 48-fold observed. Real-time demonstration of the cycloaddition mediated fluorogenic property was achieved by imaging the “turn-on” reaction within a continous flow micro-reactor. Preliminary evidence indicates that excited state quenching involves a photoinduced electron transfer.

Graphical abstract: Fluorogenic NIR-probes based on 1,2,4,5-tetrazine substituted BF2-azadipyrromethenes

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Article information


Submitted
20 Aug 2017
Accepted
12 Sep 2017
First published
13 Sep 2017

Chem. Commun., 2017,53, 10804-10807
Article type
Communication

Fluorogenic NIR-probes based on 1,2,4,5-tetrazine substituted BF2-azadipyrromethenes

D. Wu and D. F. O’Shea, Chem. Commun., 2017, 53, 10804
DOI: 10.1039/C7CC06545K

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