3 years ago

Rational design of a diaminomaleonitrile-based mitochondria – targeted two-photon fluorescent probe for hypochlorite in vivo: Solvent-independent and high selectivity over Cu2+

Rational design of a diaminomaleonitrile-based mitochondria – targeted two-photon fluorescent probe for hypochlorite in vivo: Solvent-independent and high selectivity over Cu2+
For the rational design of a solvent-independent diaminomaleonitrile (DAMN)-based fluorescent probe for monitoring ClO selectively without the interference from Cu2+, a feasible strategy is to introduce the DAMN group into a sterically crowded π-conjugated framework. The addition of ClO will recover the planarity of the molecule, change the D-π-A structure, and influence intramolecular charge transfer (ICT) efficiency in the sensing system. Inspired by this strategy, a DAMN-based Schiff base derivative (HCCN) was designed and synthesized to detect ClO with a rapid response, a large Stokes shift and moderate two-photon excitation action cross-section. HCCN was highly selective for ClO detection with no analyte interference (especially from Cu2+) in CH3CN/PBS and other mixed solvent systems. Density functional theory (DFT)/TDDFT calculations supported that the enhanced fluorescence signal of HCCN to ClO was arisen mainly from the recovery of the planar structure and the accompanying enhancement of ICT efficiency in 4. A co-staining experiment of HCCN showed its high affinity towards intracellular mitochondria; subsequently, HCCN was successfully applied for two-photon bio-imaging of exogenous ClO in fresh tissues and endogenous ClO in vivo.

Publisher URL: www.sciencedirect.com/science

DOI: S0925400517312261

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