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Synthesis and studies of phenothiazine based AIE fluorogens

By: Manav, Neha.
Contributor(s): Verma, Vani.
Publisher: New Delhi CSIR 2019Edition: Vol.58(B), Feb.Description: 238-246p.Subject(s): GENERAL CHEMISTRYOnline resources: Click here In: Indian journal of chemistry (Section B)Summary: Phenothiazine based AIE fluorogens linked to phenyl and tetraphenylethylene groups are reported. The N-butylphenothiazine and N-phenylphenothiazine have been substituted at 3,7-positions with phenyl or tetraphenylethylene (TPE) groups. All the target molecules have been characterized by 1H and 13C NMR, and mass spectrometry. The UV-Vis absorption, fluorescence and aggregation induced emission (AIE) properties of target molecules have been studied. Typically, the phenyl and TPE substituted phenothiazine molecules exhibit strong absorption band (λabs = 331 to 358 nm) in THF. Also, weak emission is observed in THF (λem = 405 to 531 nm) for these compounds; due to AIE phenomenon in water/THF mixture (fw≥70%) the emission intensity is drastically enhanced upon aggregation. Bioimaging studies in A549 cells reveal cytoplasmic distribution of the 3,7-diphenylphenothiazine derivatives with ≥ 90% cell viability.
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Phenothiazine based AIE fluorogens linked to phenyl and tetraphenylethylene groups are reported. The N-butylphenothiazine and N-phenylphenothiazine have been substituted at 3,7-positions with phenyl or tetraphenylethylene (TPE) groups. All the target molecules have been characterized by 1H and 13C NMR, and mass spectrometry. The UV-Vis absorption, fluorescence and aggregation induced emission (AIE) properties of target molecules have been studied. Typically, the phenyl and TPE substituted phenothiazine molecules exhibit strong absorption band (λabs = 331 to 358 nm) in THF. Also, weak emission is observed in THF (λem = 405 to 531 nm) for these compounds; due to AIE phenomenon in water/THF mixture (fw≥70%) the emission intensity is drastically enhanced upon aggregation. Bioimaging studies in A549 cells reveal cytoplasmic distribution of the 3,7-diphenylphenothiazine derivatives with ≥ 90% cell viability.

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