Runsheng Jiang

Synthesis and Self‐Assembly of Dihydroxyperylene Bisimides for the Tuning of Photophysical Properties

The synthesis of 1,10-dihydroxyperylene bisimides by nucleophilic substitution of brominated perylene bisimide is described. 1,10-Dihydroxyperylene bisimides formed J aggregates in nonpolar solvents and showed a clearly redshifted absorption band. The solvent polarity also influenced the hydrogen bond with the hydroxyl group, and thus, the photophysical properties of perylene bisimide. The photophysical properties of these dihydroxyperylene perylene bisimides can also be tuned by changing charge transfer from the hydroxyl groups to the perylene core through the introduction of metal ions.

A “clicked” porphyrin cage with high binding affinity towards fullerenes

A cage-structured receptor was synthesized in a facile “clicked” way and showed high affinity for fullerenes and differentiated rates of binding to C60 and C70.

Designed synthesis and supramolecular architectures of furan-substituted perylene diimide.

Novel furan-substituted perylene diimides are successfully synthesized and an efficient supramolecular architecture approach to construct zero/one-dimensional nano- and micro-structures by controlling solvents has been demonstrated. The aggregate structure conversion in different molecular structures can be controlled in the form of sphere-like, rod-like, and vesicle-like structures. As expected, these solid supramolecular rod-like architectures displayed interesting optical waveguide behavior, which indicates the aggregate structure materials of furan-substituted perylene diimides have the potential application as micro-scale photonic elements.

Synthesis of a naphthalenediimide-based cyclophane for controlling anion–arene interactions

A cationic cyclophane based on a photoactive naphthalenediimide (NDI) moiety and cationic triazolium units has been prepared. This system was employed to control the interactions between anions and the NDI motif and tune the charge transfer properties of the NDI with different anions. High selectivity was observed for fluoride anions, which preferred to interact with the NDI through a SOMO–LUMO-based electronic transition to form NDI radical anions in solution. This cyclophane can crystallize to form a porous lattice which allowed for a gradual leaking of PF6− anions, with replacement by smaller-sized halides. Charge transfer complexes were formed upon replacing the non-nucleophilic hexafluorophosphate anions with halides in the molecular crystals.

A chiral macrocyclic receptor for sulfate anions with CD signals

A novel macrocyclic binaphthalene derivative (L) containing amide and triazole units has been synthesized by “click” reaction. The binding behaviors of this receptor toward anions have been studied by 1H NMR titration, circular dichroism (CD) spectroscopy. The tetrahedral sulfate anion predominantly interacts with L through hydrogen bonds which could tune the dihedral angle between the two naphthalene rings and supply tunable CD output signals to form chiral receptor.

Designed Synthesis of a Highly Conjugated Hexaethynylbenzene‐Based Host for Supramolecular Architectures

The construction of efficient synthetic functional receptors with tunable cavities, and the self-organization of guest molecules within these cavities through noncovalent interactions can be challenging. Here we have prepared a double-cavity molecular cup based on hexaethynylbenzene that possesses a highly π-conjugated interior for the binding of electron-rich guests. X-ray crystallography, NMR spectroscopy, UV/Vis spectroscopy, fluorescent spectroscopy, cyclic voltammetry, and SEM were used to investigate the structures and the binding behaviors. The results indicated that the binding of a guest in one cavity would affect the binding of the same or another guest in the other cavity. The effect of electron transfer in this system suggests ample opportunities for tuning the optical and electronic properties of the molecular cup and the encapsulated guest. The encapsulation of different guests would also lead to different aggregate nanostructures, which is a new way to tune their supramolecular architectures.