Efficient one-pot synthesis of pyrrolylBODIPY dyes

18 Oct 2012

A straightforward route to synthesize pyrrolylBODIPY dyes, which can be used for fluorescent imaging, from acid chloride and excess pyrrole has been developed by scientists in China.

Pyrrolyldipyrromethenes contain the same core structure as the natural red pigment prodigiosin, and have received a lot of interest due to their broad range of biological activities. When pyrrolyldipyrromethene is complexed with boron, the result is long wavelength absorbing and emitting fluorescent dyes. In the synthesis of these dyes, the key step is the synthesis of the 2,2′-bipyrrole unit which often involves multiple steps and the use of expensive catalysts.

In this work, Erhong Hao, Lijuan Jiao and colleagues from Anhui Normal University, China, report that by reacting acyl chloride and excess pyrrole in dichloromethane under an oxygen atmosphere, to give the pyrrolylBODIPY dyes after about 10 hours. The application of these dyes to the fluorescent imaging of living-cells was then tested and the results suggested that the dyes were non-toxic and could easily be taken up by the cells.

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One-pot efficient synthesis of pyrrolylBODIPY dyes from pyrrole and acyl chloride, Min Zhang, Erhong Hao, Yajun Xu, Shengzhou Zhang, Hongnian Zhu, Qi Wang, Changjiang Yu and Lijuan Jiao, RSC Adv., 2012, DOI: 10.1039/C2RA22203E