Abstract
Nanographenes have kindled considerable interest in the fields of materials science and supramolecular chemistry as a result of their unique self-assembling and optoelectronic properties. Encapsulating the contorted nanographenes inside artificial receptors, however, remains challenging. Herein, we report the design and synthesis of a trigonal prismatic hexacationic cage, which has a large cavity and adopts a relatively flexible conformation. It serves as a receptor, not only for planar coronene, but also for contorted nanographene derivatives with diameters of approximately 15 Å and thicknesses of 7 Å. A comprehensive investigation of the host-guest interactions in the solid, solution and gaseous states by experimentation and theoretical calculations reveals collectively an induced-fit binding mechanism with high binding affinities between the cage and the nanographenes. Notably, the photostability of the nanographenes is improved significantly by the ultrafast deactivation of their excited states within the cage. Encapsulating the contorted nanographenes inside the cage provides a noncovalent strategy for regulating their photoreactivity.
Highlights
Nanographenes have kindled considerable interest in the fields of materials science and supramolecular chemistry as a result of their unique self-assembling and optoelectronic properties
Nanographenes[1,2,3,4] (NGs), a class of large polycyclic aromatic hydrocarbons (PAHs) that extend over 1.0 nm[5], have attracted considerable attention both in the scientific community and in technological spheres on account of their unique selfassembling[6,7], redox[8], and optoelectronic properties[9,10,11]
In attempts to modulate the dimensions of CBPQT4+, the 1,4-disubstituted phenylene rings have been replaced by 1,3,5-trisubstituted benzenoid ones in order to obtain cage-like cyclophanes[56], such as, ExCage6+ (Fig. 1b), which exhibits higher complexation strengths towards a series of neutral PAHs
Summary
Nanographenes have kindled considerable interest in the fields of materials science and supramolecular chemistry as a result of their unique self-assembling and optoelectronic properties. We report the design and synthesis of a trigonal prismatic hexacationic cage, which has a large cavity and adopts a relatively flexible conformation It serves as a receptor, for planar coronene, and for contorted nanographene derivatives with diameters of approximately 15 Å and thicknesses of 7 Å. Designing an artificial receptor, with the property of high binding affinities toward nanographenes and protecting them from photo-degradation, is a challenging, yet worthwhile, objective in noncovalent synthesis Macrocyclic arenes, such as calix[n]arenes[45], calixpyrroles[46,47], cyanostars[48,49], and pillar[n]arenes[50,51], represent a rapidly growing family of molecular receptors that play a crucial role in supramolecular chemistry by virtue of their properties of molecular recognition towards various guests. As a consequence of the ultrafast energy transfer between the host and guests, the photostability of c-HBC guests is significantly improved within the cavity of TPACage6+, as confirmed by femtosecond transient absorption spectroscopy
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
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.
