Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band.
نویسندگان
چکیده
Non-concerted [2+2] and [4+2] cycloadditions between N,N-dimethylanilino-substituted 1,1,2,4,4-pentacyanobuta-1,3-diene and 4-ethynyl-N,N-dimethylaniline are controlled by solvent polarity and provide access to a highly functionalised 6,6-dicyanopentafulvene featuring an intense, low-energy charge-transfer band and to an unusual spirocyclic zwitterion, characterised by X-ray analysis.
منابع مشابه
Nitro-functionalized oligothiophenes as a novel type of electroactive molecular material: spectroscopic, electrochemical, and computational study.
A novel series of terthiophenes bearing electron-donor and electron-acceptor groups at the end alpha-positions has been prepared. The analysis of the UV-vis, infrared, and Raman spectra, performed with the aid of density functional theory calculations, shows that the asymmetrically substituted nitro compounds PhT(3)NO(2) and BrT(3)NO(2) behave as push-pull systems and present an intense photoin...
متن کاملHeteroleptic diimine copper(I) complexes with large extinction coefficients: synthesis, quantum chemistry calculations and physico-chemical properties.
Using the HETPHEN approach, five new heteroleptic copper(I) complexes composed of a push-pull 4,4'-styryl-6,6'-dimethyl-2,2'-bipyridine ligand and a bulky bis[(2-diphenylphosphino)phenyl]-ether (DPEphos) or a bis2,9-mesityl phenanthroline (Mes2Phen) were prepared and characterized by electronic absorption spectroscopy, electrochemistry, and TD-DFT calculations. These complexes exhibit very inte...
متن کاملFluorescence and two-photon absorption of push-pull aryl(bi)thiophenes: structure-property relationships.
Photophysical and TPA properties of series of push-pull aryl(bi)thiophene chromophores bearing electron-donating (D) and electron-withdrawing (A) end-groups of increasing strength are presented. All compounds show an intense intramolecular charge transfer (ICT) absorption band in the visible region. Increasing the D and/or A strength as well as the length of the conjugated path induces bathochr...
متن کاملA novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2 + 2] cycloaddition with alkynes.
A series of donor-acceptor molecules, featuring intense low-energy intramolecular charge-transfer bands, was prepared by regioselective [2 + 2] cycloaddition between 7,7,8,8-tetracyanoquinodimethane (TCNQ) and N,N-dialkylanilino-substituted (DAA-substituted) alkynes, followed by ring opening of the initially formed cyclobutenes.
متن کاملExcitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets.
Two-dimensional (2D) transition metal chalcogenides such as 2D MoS2 are considered prime candidate materials for the design of next generation optoelectronics. Functionalisation of these materials is considered to be a key step in tailoring their properties towards specific applications and unlocking their full potential. Here we present a van der Waals functionalisation strategy for creating M...
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 47 15 شماره
صفحات -
تاریخ انتشار 2011