jo901014w_si_002.pdf (40.01 kB)

The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System

Download (40.01 kB)
journal contribution
posted on 07.08.2009 by Ismael J. Arroyo, Rongrong Hu, Gabriel Merino, Ben Zhong Tang, Eduardo Peña-Cabrera
Fully unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) 1 was prepared. Reaction of 8-thiomethylbodipy 2 with triethylsilane in the presence of a catalytic amount of Pd and a stoichiometric amount of copper(I) thienyl-2-carboxylate (CuTC) in THF at 55 °C gave compound 1 in nearly quantitative yield. This compound displays high quantum yields (up to 93%) in polar solvents including water. Its optical properties and crystal structure are discussed.