Substitution effects in distyryl BODIPYs for near infrared organic photovoltaics

Unravelling the excited state dynamics of monofunctionalized mono- and distyryl-BODIPY and perylenediimide dyads

“…13 The efficiency of light-harvesting can be enhanced by harnessing excitonic coupling among the chromophores, which has been recently reported for cyclic BODIPY derivatives. 14 Their spectral profile can be tuned to bathochromic shifts by various structural modifications, and common strategies include functionalization at the b-position, [15][16][17] fusing aromatic rings to the pyrrole moieties 18,19 or functionalization through the C-3 and C-5 positions [20][21][22] of BODIPY to extend the conjugation. The methyl groups on the C-3 and C-5 position of BODIPY undergo facile Knoevenagel condensation reactions yielding monostyryl-BODIPY (MSBDP) and distyryl-BODIPY (DSBDP) derivatives, resulting in extension of p-conjugation and hence bathochromically shifted absorption and emission compared to core-unsubstituted BODIPY.…”

“…The methyl groups on the C-3 and C-5 position of BODIPY undergo facile Knoevenagel condensation reactions yielding monostyryl-BODIPY (MSBDP) and distyryl-BODIPY (DSBDP) derivatives, resulting in extension of p-conjugation and hence bathochromically shifted absorption and emission compared to core-unsubstituted BODIPY. [20][21][22] They have been utilized for multiple applications such as near-infrared (NIR) fluorescent probes, 23,24 light-harvesting antennae, 25,26 metal ion sensors, 27,28 solar concentrators, 29 photodynamic therapy, 30 triplet photosensitizers 31,32 and photoredox catalysis 33 because of their high absorption coefficient, NIR absorption, high fluorescence quantum yield and photostability. However, interestingly all styryl-BODIPY (STBDP) compounds reported so far are disubstituted at the b-positions, and no examples of b-monofunctionalized styryl BODIPYs are reported.…”

Reprograming cancer cells by a BODIPY G-quadruplex stabiliser

“…BODIPY compounds can be modulated to extend the π-conjugation, to attach functional groups, and to optimise the chemical and photophysical properties for many applications. 29 Previously, we have shown the potential use of the pyridinium functionalized BODIPY structures for use as G4 stabilisers and gene expression regulators. 6 a Cationic pyridinium structures both enable binding to negatively-charged phosphates of DNA, and also enhance solubility in aqueous media.…”