1357003-99-6Relevant articles and documents
Synthesis and reactivity of 4,4-dialkoxy-bodipys: An experimental and computational study
Nguyen, Alex L.,Bobadova-Parvanova, Petia,Hopfinger, Melissa,Fronczek, Frank R.,Smith, Kevin M.,Vicente, M. Gra?a H.
, p. 3228 - 3236 (2015)
A series of boron-disubstituted O-BODIPYs were synthesized, and their structures and spectroscopic properties were investigated using both computational and experimental methods. Three methods were investigated for the preparation of 4,4-dimethoxy-BODIPYs bearing electron-donating or electron-withdrawing 8-aryl groups: method A employs refluxing in the presence of NaOMe/MeOH, method B uses AlCl3 in refluxing dichloromethane followed by addition of methanol as nucleophile, and method C involves activation of the BODIPYs using TMSOTf in refluxing toluene followed by addition of methanol. The yields obtained depend on the method used and the structure of the starting BODIPYs; for example, 1a and 3a were most efficiently prepared using method C (98 and 70%, respectively), while 2a was best prepared by method A (50%). Methods B and C were employed for the synthesis of seven new 4,4-dialkoxy-BODIPYs. 4,4-Dipropargyloxy-BODIPY 1e reacted under Cu(I)-catalyzed alkyne-azide Huisgen cycloaddition conditions to produce 4,4-bis(1,2,3-triazole)-BODIPY 4 in 78% yield. The substitution of the fluorides for alkoxy groups on the BODIPYs had no significant effect on the absorption and emission wavelengths but altered their fluorescence quantum yields. Among this series of dialkoxy-BODIPYs, the 4,4-dipropargyloxy 1e and its corresponding bis(1,2,3-triazole) 4 show the largest quantum yields in toluene and THF, respectively.
Heavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction
Hu, Wenbin,Lin, Yanhe,Zhang, Xian-Fu,Feng, Mingna,Zhao, Siwen,Zhang, Jing
, p. 139 - 147 (2019/01/24)
To test the tunability of charge transfer (CT)-based BODIPY photosensitizers in generating singlet oxygen (1Δg), twelve meso-phenyl-BODIPY (donor-acceptor) type compounds have been synthesized and fully characterized, in which the ph
Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs
Gibbs, Jaime H.,Robins, Larry T.,Zhou, Zehua,Bobadova-Parvanova, Petia,Cottam, Michael,McCandless, Gregory T.,Fronczek, Frank R.,Vicente, M. Gra?a H.
, p. 5770 - 5781 (2013/09/12)
A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalizat
