915768-70-6Relevant academic research and scientific papers
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 (2015/04/14)
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.
Convenient one-pot procedure for synthesizing 4,4′-dimethoxy- boradiaza-s-indacene dyes and their application to cell labeling
Liu, Kuan-Miao,Tsai, Ming-Shan,Jan, Ming-Shiou,Chau, Chi-Min,Wang, Wan-Ju
experimental part, p. 7919 - 7922 (2011/11/06)
We succeeded in developing a convenient one-pot pathway for synthesizing 4,4′-dimethoxy-boradiaza-s-indacene dyes 4a-d. The structures feature two methoxy groups in place of the fluorine atoms in 4,4′-difluoro-4- boradiaza-s-indacene. These novel dyes emi
