A versatile synthetic approach to design tailor-made push-pull chromophores with intriguing and tunable photophysical signatures

Fully Functionalizable β,β′-BODIPY Dimer: Synthesis, Structure, and Photophysical Signatures

“…Reports on the reactivity, functionalization, applications, and structural studies of borondipyrromethenes (BODIPYs) are far from being exhausted. Note that most of what has been developed deals with monomeric BODIPYs 1 and their fascinating properties (i.e., large extinction coefficients, high quantum yields, excellent solubility in most organic solvents, resistant to photobleaching). − Additionally, they can be tailor-made by the functionalization of each of their positions to fine tune their properties for a desired application such as sensors (polarity, viscosity, pH), laser dyes, biotrackers, antenna systems, and photosensitizers among others. − …”

Synthesis, Photophysical Study, and Biological Application Analysis of Complex Borondipyrromethene Dyes

“…In a previous work, we concluded that the attachment of a para-nitrophenyl group at the 3-position was desirable to achieve improved fluorescence response toward the red-edge of the visible spectrum. 19 Therefore, we followed this strategy to boost the fluorescence response in the herein developed dyes leading to the compounds shown in Chart 4 . As expected, the feasible resonant interaction of such an aromatic arm with the dipyrrin core leads to an extended π-system, which explains the recorded bathochromic shift of the spectral bands, owing mainly to a lowest unoccupied molecular orbital stabilization as suggested by quantum mechanics simulations ( Figures 2 and S2 ).…”

“…All new products shown in Chart 3 fluoresce in the green region of the visible spectrum (vide infra). Being aware of the importance of preparing dyes that absorb and emit in the red region of the visible spectrum for biological applications, 18 a few analogues were prepared starting from our recently reported 19 modified Biellmann BODIPY 1b (Chart 4). The reactivity of BODIPY 1b was observed to be slightly lower than that of 1a.…”

Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core

“…392a and 392b have blue-shifted absorption and emission maxima in HEPES buffer (pH 7.4, containing 1% acetonitrile) at 25 °C (max abs = 400 nm, max em = 467 nm) compared with 34a (products 401c and 401d). 294 Following this synthetic methodology, the dipyrrin core was decorated with electron donating or withdrawing moieties in specific chromophoric positions leading to a large pool of push-pull dyes involving the 8-and 3-positions, or, when the 3,5-positions were blocked by a substituent (e.g., methyl), the 8-and 1-positions. Most of the substitution reactions of 8-methylthioBODIPYs reported to this point have been done using the original pyrrole-unsubstituted compound 34a, first reported by Biellmann et al 73 However, symmetrical 3,5-dimethyl-8-methylthioBODIPY (34b) 281b,294 and 3,5-diethyl-8-methylthioBODIPY (34c) 281b were also used occasionally (Scheme 106).…”