Related Experiment Video
Updated: Jun 18, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
Published on: August 23, 2018
Molecular aggregation behavior of perylene-bridged bis(beta-cyclodextrin) and its electronic interactions upon
Ke-Rang Wang1, Dong-Sheng Guo, Bang-Ping Jiang
1Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Abstract:
A novel water-soluble perylene bisimide derivative 1 was synthesized with two permethyl-beta-cyclodextrin grafts at the imide nitrogens, and its structure was identified by NMR, Fourier transform infrared spectroscopy (FT-IR), matrix-assisted laser desorption ionization mass spectrometry (MALDI-MS), and elemental analysis. Its aggregation behavior in water and organic solutions was further investigated by UV-vis, fluorescence, and (1)H NMR spectra, showing that 1 exhibits strong pi...pi aggregation in water. Especially, the aggregation and optical properties were comprehensively compared between the neutral form 1 and protonated form 1H(2) through concentration- and temperature-dependent UV-vis experiments. The aggregation constant of 1H(2) is almost 1 order of magnitude lower than that of 1 owing to electrostatic repulsion. On the other hand, 1H(2) exhibits better fluorescence than 1 by overcoming the photoinduced electron transfer process from imino groups to perylene backbone. Furthermore, by employing the binding sites of grafted cyclodextrins to aromatic guests, pronounced electronic interactions between perylene and anthracene/pyrene guests were observed.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous overlap of p...
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

