Abstract
We synthesized an amphiphilic small molecule 1 by attaching oligo(ethylene glycol) (OEG) and N,N-diethylamine (DEA) units to a fluorescent dicyanodistyrylbenzene (DCS) core. The molecule is fully soluble in aqueous solution at low pH (pH<4.3) by protonation of the DEA groups; but, above pH 4.3, it self-assembles to form nanoparticles due to increased hydrophobicity upon deprotonation, leading to a ratiometric fluorescence color change from green emission in the monomeric form (λem,max=538 nm) to red emission in the aggregated form (λem,max=646 nm). It should be noted that the ratio of emission intensities at 538 nm and 646 nm (R=I538/I646) changes drastically about 42-fold within a very narrow pH range of 4.3–4.6.
Original language | English |
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Pages (from-to) | 393-397 |
Number of pages | 5 |
Journal | ChemPhotoChem |
Volume | 4 |
Issue number | 6 |
DOIs | |
Publication status | Published - 2020 Jun 1 |
Externally published | Yes |
Keywords
- amphiphiles
- bioimaging
- fluorescence switching
- pH responsiveness
- self-assembly
- supramolecular chemistry
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Analytical Chemistry