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Synthesis of BR2 complexes of α-pyrrolyl dipyrrins

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Abstract A series of BR2 complexes of α-pyrrolyl dipyrrin were synthesized from BF2 complex of α-pyrrolyl dipyrrin (3-pyrrolyl BODIPY) by treating it with various alkyl- and aryl magnesium halides under… Click to show full abstract

Abstract A series of BR2 complexes of α-pyrrolyl dipyrrin were synthesized from BF2 complex of α-pyrrolyl dipyrrin (3-pyrrolyl BODIPY) by treating it with various alkyl- and aryl magnesium halides under mild Grignard reaction conditions. The BR2 complexes were functionalized at α-position of the appended pyrrole ring with formyl, chloro and bromo functional groups and these functionalized BR2 complexes were used further to prepare various novel derivatives of BR2 complexes. The BR2 complexes were characterized by HR mass, NMR, absorption, fluorescence, and electrochemical techniques. Two of the BR2 complexes were structurally characterized by X-ray crystallography. Our studies revealed that the substitution of fluorine atoms at the boron center of 3-pyrrolyl BODIPYs with different alkyl/aryl groups significantly alters their structural, spectral and electrochemical properties. The DFT studies also support the alteration of the electronic properties of the BR2 complexes.

Keywords: br2 complexes; br2; complexes pyrrolyl; synthesis br2; pyrrolyl dipyrrins

Journal Title: Tetrahedron
Year Published: 2019

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