1301766-06-2Relevant academic research and scientific papers
An Autocatalytic System of Photooxidation-Driven Substitution Reactions on a FeII4L6 Cage Framework
Neelakandan, Prakash P.,Jiménez, Azucena,Thoburn, John D.,Nitschke, Jonathan R.
supporting information, p. 14378 - 14382 (2016/01/25)
The functions of life are accomplished by systems exhibiting nonlinear kinetics: autocatalysis, in particular, is integral to the signal amplification that allows for biological information processing. Novel synthetic autocatalytic systems provide a foundation for the design of artificial chemical networks capable of carrying out complex functions. Here we report a set of FeII4L6 cages containing BODIPY chromophores having tuneable photosensitizing properties. Electron-rich anilines were observed to displace electron-deficient anilines at the dynamic-covalent imine bonds of these cages. When iodoaniline residues were incorporated, heavy-atom effects led to enhanced 1O2 production. The incorporation of (methylthio)aniline residues into a cage allowed for the design of an autocatalytic system: oxidation of the methylthio groups into sulfoxides make them electron-deficient and allows their displacement by iodoanilines, generating a better photocatalyst and accelerating the reaction.
Highly Regioselective α-Chlorination of the BODIPY Chromophore with Copper(II) Chloride
Zhou, Xin,Yu, Changjiang,Feng, Zeya,Yu, Yang,Wang, Jun,Hao, Erhong,Wei, Yun,Mu, Xiaolong,Jiao, Lijuan
supporting information, p. 4632 - 4635 (2015/09/28)
A general and efficient method for α-chlorination of 4,4′-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) has been developed using CuCl2 as chlorination reagent. The reaction is characterized by complete 3/5-positions of BODIPY regioselectivity. This unusual highly regioselective α-halogenation of BODIPY is in sharp contrast to previously reported halogenation methods which preferred to occur first at the 2,6-positions of BODIPY. This approach provides a straightforward, facile, and economical route to 3- and/or 5-chloroBODIPYs with various meso-groups (H, alkyl, and aryl) and their derivatives.
Fluorophore incorporation allows nanomolar guest sensing and white-light emission in M4L6 cage complexes
Neelakandan, Prakash P.,Jimenez, Azucena,Nitschke, Jonathan R.
, p. 908 - 915 (2014/03/21)
We have prepared a series of M4L6 tetrahedral cages containing BODIPY and pyrene moieties and followed their guest-binding properties through electronic absorption and fluorescence spectroscopies. Our results indicate that these cage
Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura coupling
Hayashi, Yosuke,Yamaguchi, Shigeru,Cha, Won Young,Kim, Dongho,Shinokubo, Hiroshi
supporting information; experimental part, p. 2992 - 2995 (2011/08/03)
Treatment of a meso-arylboron dipyrrin (BODIPY) with NBS provides mono- and dibrominated BODIPYs at the 2- and 6-positions in excellent yields with high regioselectivity. Brominated products can be employed as a nice building block for the synthesis of a
