Photophysical and electrochemical properties of sterically crowded polyarylated boron-dipyrromethenes

• Published in: Chemical physics letters 2013-03, Vol.564, p.93-97
• Main Authors: Lakshmi, Vellanki, Ravikanth, Mangalampalli
• Format: Article
• Language: English
• ISSN: 0009-2614; 1873-4448
• DOI: 10.1016/j.cplett.2013.02.023

The effect of aryl groups at all pyrrole carbons of BODIPY core on absorption, fluorescence and electrochemical properties of BODIPY dye in polyarylated BODIPYs were investigated. [Display omitted] ► Aryl substituents at pyrrole carbons of BODIPY alters the electronic properties. ► Large bathochromic shifts in absorption and emission bands. ► Large Stokes shifts, good quantum yields and singlet state lifetimes. ► Stable under redox conditions. ► Aryl substituents prevent aggregation in solid state and result in strong fluorescence. The absorption, fluorescence and electrochemical properties of six polyarylated BODIPYs were investigated in solution. The presence of aryl substituents at all pyrrole carbons of BODIPY significantly alters the electronic properties of the dye. Compared to unsubstituted meso-aryl BODIPY, the polyarylated BODIPYs exhibited large bathochromic shifts in absorption and emission bands, large Stokes shifts, fluorescence quantum yields and singlet state lifetimes. These changes are attributed to the aryl groups which create steric crowding and induces nonplanarity in the BODIPY core altering the electronic properties of the dyes. The polyarylated BODIPYs were stable under redox conditions and exhibited reversible/quasi-reversible oxidation and reduction.