Rational design of visible and NIR distyryl-BODIPY dyes from a novel fluorinated platform

Abstract

A new series of distyryl-BODIPY has been rationally designed and synthesised from a novel fluorinated platform, 8-pentafluorophenylBODIPY, which has enhanced reactivity in the presence of both electron rich, and for the first time, electron deficient aldehydes. The pentafluorobenzene leads to larger red shifts of absorption and emission compared to previously reported analogues. The reactivity and spectroscopic results have been rationalised with quantum mechanics calculation. The fluorescence sensitivity of one derivative to acidity is also presented.

Synthesis and Optical Properties of Difluorobora‐s‐diazaindacene Dyes with Trifluoromethyl meso‐Substituents

“…[16] The step represents the P 2 O 5 -promoted condensation of available 2,2,2-trifluoro-1-(pyrrol-2yl)-1-ethanols with pyrroles. It should be noted that this methodology makes it possible to synthesize both symmetrical and asymmetrical BODIPYs as opposed to other methods [14,15] affording exclusively symmetrical BODIPYs.…”

“…[13] This approach allows both absorption and emission to be shifted by 100-200 nm towards red. Very important shifts towards the NIR end of the visible spectra have been recently achieved by introducing a strong electron acceptor such as pentafluorobenzene [14] or CF 3 [15,16] at the meso-position of the BODIPY core, though the asymmetrical representatives with a meso-CF 3 moiety can only be synthesized by using a specific methodology. [16] We have concisely reported that the presence of a CF 3 group in the meso-position of the BODIPY core does cause a deep bathochromic shift relative to congeners with other substituents in this position.…”

Development of lipopolyplexes for gene delivery: A comparison of the effects of differing modes of targeting peptide display on the structure and transfection activities of lipopolyplexes

“…Thus, the sequence CK 16 was site‐selectively labelled with a fluorophore as follows. A perfluoro‐BODIPY functionalised in the para‐position of the perfluorophenyl ring was reacted via a nucleophilic aromatic substitution to give maleimido‐F4‐BODIPY. This was then conjugated to CK 16 to give peptide P8 (F4‐BODIPY‐CK 16 ).…”

The Synthesis, Characterization, Crystal Structure and Photophysical Properties of a New Meso-BODIPY Substituted Phthalonitrile

“…Characterization of the products was carried out by a combination of methods including FT-IR, 1 H NMR, 13 vibration at 3158 cm −1 and the appearance of new absorption bands at 2237 and 1255 cm −1 belonging to the -C≡N and Ar-O-Ar respectively, clearly indicate the formation of 1.…”

“…This kind of substitutions can have a strong influence on the position of the absorption and emission maxima which range from at about 500 nm to over 700 nm depending on their location on the BODIPY core [13,14].…”