Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 8, Issue 3, Pages 564-571Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201201009
Keywords
fluorescence; nonlinear optics; quadrupolar derivatives; terpyridine; two-photon absorption
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Funding
- Singapore Ministry of Education through the Academic Research Fund (Tier 1) [RG63/10]
- Singapore National Research Foundation through the Competitive Research Programme (CRP) [NRF-CRP5-2009-04]
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Developing organic chromophores with large two-photon absorption (TPA) in both organic solvents and aqueous media is crucial owing to their applications in solid-state photonic devices and biological imaging. Herein, a series of novel terpyridine-based quadrupolar derivatives have been synthesized. The influences of electron-donating group, type of conjugated bridge, as well as solvent polarity on the molecular TPA properties have been investigated in detail. In contrast to the case in organic solvents, bis-(thienyl)-benzothiadiazole as a rigid conjugated bridge will completely quench molecular two-photon emission in aqueous media. However, the combination of alkylcarbazole as the donor and bisACHTUNGTRENUNG(styryl) benzene as a conjugation bridge can enlarge molecular TPA cross-sections in both organic solvent and aqueous media. The reasonable two-photon emission brightness for the organic nanoparticles of chromophores 3-5 in the aqueous media, prepared by the reprecipitation method, enables them to be used as probes for in vivo biological imaging.
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