Oxidation of 2-amino-substituted BODIPYs providing pyrazine-fused BODIPY trimers.
نویسندگان
چکیده
Oxidation of 2-amino-substituted BODIPYs afforded BODIPY trimers in a one-step operation. The trimer consists of a pyrazine-fused BODIPY dimer to which one BODIPY unit is connected through an NH linkage. Effective expansion of π-conjugation over the fused dimer was observed in optical and electrochemical measurements.
منابع مشابه
Synthesis, photophysical, electrochemical, and electrogenerated chemiluminescence studies. Multiple sequential electron transfers in BODIPY monomers, dimers, trimers, and polymer.
Synthesis of the C(8) BODIPY monomers, dimers, and trimers, a C(8) polymer, and N(8) aza-BODIPY monomer and dimer was carried out. Methyl and mesityl C(8)-substituted monomers, dimers, and trimers were used. Dimers, trimers, and polymer were formed chemically through the β-β (2/6) positions by oxidative coupling using FeCl(3). A red shift of the absorbance and fluorescence is observed with addi...
متن کاملMeso enamine substituted BODIPYs.
Different enamines were introduced at the meso position of the BODIPY by catalyst free oxidation of tert-amines and in situ cross coupling with 8-chloro BODIPY. The reaction conditions were optimized to achieve better yields. The reaction works well with aliphatic tert-amines bearing an N-(CH-CH-) backbone. The N-alkyl substituents perturb the optical properties of enamine substituted BODIPYs.
متن کاملThiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives.
A high-yielding method for the direct thiocyanation of BODIPY dyes is described. In 1,3-dimethyl BODIPYs, the thiocyanato group adds at position 2, whereas the insertion occurs at position 5 in 3-amino BODIPYs. The transformation of the thiocyanato group enables the synthesis of thioalkylated BODIPYs. 2-Thioalkylated BODIPYs and 3-thiocyanato-5-piperidino BODIPYs exhibit interesting spectroscop...
متن کاملTetracyanobutadiene functionalized ferrocenyl BODIPY dyes.
Tetracyanobutadiene (TCBD) derivatives of ferrocenyl BODIPYs 2a-2c were designed and synthesized by [2 + 2] cycloaddition-retroelectrocyclization reaction of tetracyanoethylene (TCNE) with meso alkynylated ferrocenyl BODIPYs. The TCBD substituted ferrocenyl BODIPYs were designed in such a way that the distance between the ferrocenyl unit and the TCBD remains constant, whereas the distance betwe...
متن کاملπ-Fused bis-BODIPY as a candidate for NIR dyes.
Benzene-fused bis-(borondipyrromethene)s (bis-BODIPYs) were synthesized by retro-Diels-Alder reaction of the corresponding bicyclo[2.2.2]octadiene-fused (BCOD-fused) bis-BODIPYs, which were, in turn, prepared from 4,8-ethano-4,8-dihydropyrrolo[3,4-f]isoindole derivatives. The π-fused bis-BODIPY chromophores were designed to show intensive absorption and strong fluorescence in the near-infrared ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 50 21 شماره
صفحات -
تاریخ انتشار 2014