AIE active piperazine appended naphthalimide-BODIPYs: photophysical properties and applications in live cell lysosomal tracking

Piperazine appended naphthalimide-BODIPYs (NPB1-NPB4) exhibiting solvatochromism and aggregation-induced emission with a large Stokes shift (up to 146 nm) have been described. Separation of naphthalimide and BODIPY fluorophores by piperazine in these conjugates creates a donor-acceptor system and in...

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Bibliographic Details
Published in:Analyst (London) 2019-01, Vol.144 (1), p.331-341
Main Authors: Dwivedi, Bhupendra Kumar, Singh, Roop Shikha, Ali, Afsar, Sharma, Vinay, Mobin, Shaikh M, Pandey, Daya Shankar
Format: Article
Language:English
Subjects:
Biocompatibility
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Boron Compounds - radiation effects
Boron Compounds - toxicity
Charge transfer
Chemical compounds
Conjugates
Electron transfer
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Fluorescent Dyes - radiation effects
Fluorescent Dyes - toxicity
HeLa Cells
Humans
Hydrogen-Ion Concentration
Light
Lysosomes - metabolism
Molecular Structure
Naphthalimides - chemical synthesis
Naphthalimides - chemistry
Naphthalimides - radiation effects
Naphthalimides - toxicity
Piperazines - chemical synthesis
Piperazines - chemistry
Piperazines - radiation effects
Piperazines - toxicity
Spectrometry, Fluorescence
Tracking
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Summary:Piperazine appended naphthalimide-BODIPYs (NPB1-NPB4) exhibiting solvatochromism and aggregation-induced emission with a large Stokes shift (up to 146 nm) have been described. Separation of naphthalimide and BODIPY fluorophores by piperazine in these conjugates creates a donor-acceptor system and induces twisted intramolecular charge transfer, in addition to photoinduced electron transfer. The crucial role of naphthalimide, the alkyl chain length, the piperazine ring, and the solid-state packing on AIE has been extensively investigated by various studies. Superior cell permeability coupled with bio-compatibility of these conjugates offers a unique opportunity for their potential applications in live cell lysosomal tracking.
ISSN:0003-2654
1364-5528
DOI:10.1039/c8an01390j