Abstract
Conjugation of nanographenes (NGs) with electro-active molecules can establish donor-acceptor π-systems in which the former generally serve as the electron-donating moieties due to their electronic-rich nature. In contrast, here we report a series of reversed donor-acceptor structures are obtained by C–N coupling of electron-deficient perchlorinated NGs with electron-rich anilines. Selective amination at the vertexes of the NGs is unambiguously shown through X-ray crystallography. By varying the donating ability of the anilino groups, the optical and assembly properties of donor-acceptor NGs can be finely modulated. The electron-deficient concave core of the resulting conjugates can host electron-rich guest molecules by intermolecular donor-acceptor interactions and gives rise to charge-transfer supramolecular architectures.
Highlights
Conjugation of nanographenes (NGs) with electro-active molecules can establish donoracceptor π-systems in which the former generally serve as the electron-donating moieties due to their electronic-rich nature
The concave molecular structures of these D-A NGs are clearly demonstrated by single-crystal X-ray diffraction, which show a selective amination at the vertexes
Different from previously reported concave polycyclic aromatic hydrocarbons, the concave electron-deficient skeletons of the D-A NGs can assemble with donor-type guest molecules such as tetrathiafulvalene by intermolecular charge transfer (CT)
Summary
Conjugation of nanographenes (NGs) with electro-active molecules can establish donoracceptor π-systems in which the former generally serve as the electron-donating moieties due to their electronic-rich nature. A few studies have switched the electronic characteristics of NGs from electron-rich to electron-poor by multiple introduction of strongly electronwithdrawing groups, such as bisimide[26,27,28,29], chloro[30], and fluoro[31, 32] substituents Such electron-deficient NGs provide alternative pathway to D-A conjugates. We report an amination occurring at the vertexes of perchlorinated NGs by palladium-catalyzed Buchwald–Hartwig coupling[33, 34] Using this strategy, various electron-rich aniline derivatives are coupled to the periphery of electron-deficient chlorinated NGs, providing a series of nano-sized D-A architectures. Different from previously reported concave polycyclic aromatic hydrocarbons, the concave electron-deficient skeletons of the D-A NGs can assemble with donor-type guest molecules such as tetrathiafulvalene by intermolecular charge transfer (CT)
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
