Donor-acceptor complexes of dipyrrolylmethenes with boron trifluoride as intermediates in the synthesis of Bodipy

作者：Rumyantsev E V^*; Marfin Yu S; Antina E V

来源：Russian Chemical Bulletin, 2010, 59(10): 1890-1895.

DOI：10.1007/s11172-010-0329-3

• donor-acceptor complexes (DAC)
• dipyrrolylmethenes
• boron trifluoride
• Bodipy complexes
• stability
• mechanism of formation
• electronic absorption spectroscopy
• IR spectroscopy
• (1)H NMR spectroscopy
• semiempirical methods

The formation of donor-acceptor complexes of dipyrrolylmethene and structurally similar biladiene-a,c with boron trifluoride was studied by electronic absorption, IR, and (1)H NMR spectroscopies as well as by quantum chemical calculations. It was shown that the formation of donor-acceptor complexes is the first step of the synthesis of the corresponding boron fluoride chelate complexes (Bodipy). The hydrogen bond N-H...F-B additionaly stabilizes the donor-acceptor complexes. The stability constants, geometric parameters, and energy characteristics of the donoracceptor complexes were determined; the two-step mechanism of Bodipy synthesis was analyzed.

• 出版日期2010-10