High Yield S_NAr on 8‐Halogenophenyl‐BODIPY with Cyclic and Acyclic Polyamines

Abstract

Selective nucleophilic aromatic substitutions with several polyamines were performed in very good yields on halogeno‐phenyl BODIPY derivatives containing an activating nitro group.

Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril

“…Surprisingly, and despite the hexaalkylated core was used, the fluorescence quantum yields of protonated as well as unprotonated 3 were more than 100-fold lower than the quantum yields of the other derivatives. Such reduced quantum yields have been previously reported for some BODIPYs substituted with diamines in the aniline meso -position, and the decreased quantum yields were ascribed to the loose-bolt effect [41,54–55]. …”

Synthesis of Porphyrinoids, BODIPYs, and (Dipyrrinato)ruthenium(II) Complexes from Prefunctionalized Dipyrromethanes

“…[33,45,46] Apart from some preliminary work related to the 5-(4-fluoro-3-nitrophenyl)dipyrromethene carried out in our group, [46] to the best of our knowledge only one publication has appeared on the S N Ar of 4-fluoro-3-nitrophenyl-substituted BODIPYs. The 4-fluoro-3-nitrophenyl group has received little attention as a substituent in BODIPYs and porphyrinoids.…”

“…[33,45,46] Apart from some preliminary work related to the 5-(4-fluoro-3-nitrophenyl)dipyrromethene carried out in our group, [46] to the best of our knowledge only one publication has appeared on the S N Ar of 4-fluoro-3-nitrophenyl-substituted BODIPYs. In contrast to the harsher reaction conditions described by Volkova et al (boiling acetonitrile) for the reaction with BODIPYs, [33] milder reaction conditions were employed for the S N Ar of dipyrromethane 6 with primary amines. [33] In the first step, the dipyrromethane 6 carrying the 4-fluoro-3-nitrophenyl substituent was synthesized from 4-fluoro-3-nitrobenzaldehyde and pyrrole according to our recently published procedure (Scheme 3).…”

“…Based on this, the 4-fluoro-3-nitrophenyl group presents itself as a good alternative to the well-established pentafluorophenyl substituent, with only a few S N Ar reactions on 4-fluoro-3-nitrophenyl-substituted BODIPYs [33] and 4-fluoro-3-nitrophenyl-substituted thiadiazole [34] already described in the literature. The electron-withdrawing effect of the fluoro and the nitro group should have a comparable stabilization effect on the dipyrromethane like the pentafluorophenyl substituent.…”

Pseudo‐Crown Ethers as Novel Scaffolds for the Development of Al3+‐Selective Fluorescent Probes

“…Inspired by these works, we decided to look for pseudo‐crown ether convenient for the development of turn‐on fluorescent probes selective for Al 3+ ions. Recently, we found that diverse boron dipyrromethenes (BODIPY) functionalized with aza‐crowns and their open‐chain N , O ‐analogues exhibit rich fluorescence properties promising for the detection of heavy metal cations . Herein we report the synthesis and spectral characterization of five novel BODIPY pseudo‐crown‐based fluorescent Al 3+ ion sensor molecules.…”