Synthesis and nanoparticle encapsulation of 3,5-difuranylvinyl-boradiaza-s- indacenes for near-infrared fluorescence imaging

Sehoon Kim, Tymish Y. Ohulchanskyy, Alexander Baev, Paras N. Prasad

    Research output: Contribution to journalArticlepeer-review

    26 Citations (Scopus)

    Abstract

    We report molecular design, synthesis, and photophysical study of a series of near-infrared absorbing and fluorescing dyes, 3,5-difuranylvinyl-boradiaza-s- indacenes, bearing various 5-membered heteroaromatic heads at the 8-position (FBs). The correlation between the molecular structure and the spectral shift has been studied by quantum chemical calculations at various levels (B3LYP/6-31G*, HF/6-31G* and HF/PM3), which conclude that the planarity determined by the bulkiness of the head unit controls the optical bandgap of FBs, by energetically affecting the lowest unoccupied molecular orbital (LUMO) rather than the highest occupied molecular orbital (HOMO). We also show that incorporation of heavy atoms increased the capability of singlet oxygen generation as a result of enhanced intersystem crossing, which makes FBs potentially useful for near-infrared photodynamic therapy. In vitro near-infrared fluorescence imaging of live tumor cells has been demonstrated through a nanocarrier approach, by encapsulating one of the FB dyes in a stable aqueous formulation of organically modified silica nanoparticles which retains the fluorescence efficiency of the hydrophobic dye in water.

    Original languageEnglish
    Pages (from-to)3181-3188
    Number of pages8
    JournalJournal of Materials Chemistry
    Volume19
    Issue number20
    DOIs
    Publication statusPublished - 2009

    ASJC Scopus subject areas

    • General Chemistry
    • Materials Chemistry

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