MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyesElectronic supplementary information (ESI) available: General procedures, chemical structures and characterization data of BDC, BDCAC and BDCCA. Full characterization data (NMR, HR-MS) for BDC-9. Additional experimental data for BDC-9-HSA binding. See DOI: 10.1039/c3sc22166k

• Main Authors: Er, Jun Cheng, Tang, Mui Kee, Chia, Chee Geng, Liew, Huimin, Vendrell, Marc, Chang, Young-Tae
• Format: Article
• Language: English
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/c3sc22166k

A novel class of triazole-derivatized BODIPY compounds have been synthesized on solid-phase by employing mild reaction conditions based on the copper-catalyzed azide-alkyne cycloaddition. The resulting BODIPY-triazoles exhibited MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive quantum yield increments that asserted their potential as turn-on fluorescent sensors. Out of a library of 120 compounds, we identified BDC-9 as a fluorescent chemosensor with high sensitivity and remarkable species-selectivity towards human serum albumin. These results validate MegaStokes BODIPY dyes as new fluorophores for the development of environmentally sensitive fluorescent probes. A novel class of triazole-derivatized BODIPYs was conveniently synthesized on solid-phase with minimum purification and high purities. Compounds exhibit MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive turn-on fluorescence.