Macrocycles and cages based on tetraphenylethylene with aggregation-induced emission effect.

Chem Soc Rev

Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, China.

Published: October 2018


Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

Organic molecules with an aggregation-induced emission (AIE) effect have recently been attracting more and more attention due to their colossal potential in solid emitters and chemo/biosensors. The number and variety of AIEgen compounds are expanding very rapidly to obtain better application performance and a wider area of application. Among AIEgen systems, tetraphenylethylene (TPE) and its derivatives are the class that have received the most extensive study and the most rapid development because of their facile synthesis. Due to its C2 symmetry and at least tetratopic reaction positions, the TPE unit is also an ideal building block for constructing macrocycles and cages. The resultant cyclic TPE compounds have exhibited many exceptional performances that are difficult to access in their open chain counterparts, such as AIE enhancement, improvement in selectivity and sensitivity as sensors, emission tuning by guests, supramolecular catalysis, further disclosure of the AIE mechanism, molecular adsorption, storage and release, the propeller-like conformation exploitation of the TPE unit in chiral materials and so on. Recently, therefore, a large variety of studies about the synthesis, properties and application research of TPE macrocycles and cages have been reported. These TPE macrocycles and cages significantly expand the research area for the AIE phenomenon and its applications, and represent a development of the AIE area. However, up to now, no review of TPE macrocycles and cages has been available. Thus, this review serves as a summary of the designs, synthesis, photophysical properties, self-assembly, applications and prospects of TPE macrocycles and cages.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c8cs00444gDOI Listing

Publication Analysis

Top Keywords

macrocycles cages
24
tpe macrocycles
16
aggregation-induced emission
8
tpe
8
tpe unit
8
macrocycles
6
aie
5
cages
5
cages based
4
based tetraphenylethylene
4

Similar Publications

ConspectusCrystalline porous frameworks, such as covalent organic frameworks (COFs), metal-organic frameworks (MOFs), and hydrogen-bonded organic frameworks (HOFs), have demonstrated exceptional potential in diverse applications, including gas adsorption/separation, catalysis, sensing, electronic devices, etc. However, the building blocks for constructing ordered frameworks are typically limited to multisubstituted aromatic small molecules, and uncontrolled interpenetration has remained a long-standing challenge in the field. Shape-persistent macrocycles and molecular cages have garnered significant attention in supramolecular chemistry and materials science due to their unique structures and novel properties.

View Article and Find Full Text PDF

The design and assembly of interlocked supramolecular cages is of interest due to their exquisite topological configuration and excellent performance in a variety of applications. We introduce two carbazole-based ligands L1 and L2, they combine with four distinct half-sandwich rhodium building blocks to form three molecular-tweezer-like compounds, three interlocked cages, tetranuclear macrocycle, and hexanuclear cage. Stacking interactions between carbazole groups facilitate the formation of interlocked structures.

View Article and Find Full Text PDF

Naphthalene- and Perylene-Diimide-Based Chiral Supramolecular Architectures.

Adv Mater

August 2025

School of Materials Science and Engineering, Tianjin Key Laboratory of Metal and Molecule Based Material Chemistry, Nankai University, Tianjin, 300350, P. R. China.

Chiral supramolecular architectures based on naphthalene diimide (NDI) and perylene diimide (PDI) possess significant potential for chiroptical applications due to their physical properties, including large molar extinction coefficient, high fluorescence quantum yield, reversible redox activity, and robust photochemical/thermal stability. The chirality of NDI/PDI-based supramolecular architectures primarily originates from three sources: i) covalent modification of NDI/PDI with chiral substituents, ii) intrinsic axial chirality through distortion of the PDI conjugated plane, and iii) supramolecular asymmetric assembly of achiral NDI/PDI induced by exogenous chiral environments. This review systematically outlines recent advancements in the design principles of NDI/PDI-based chiral supramolecular architectures, including macrocycles, cages, aggregates, and crystalline frameworks, with an emphasis on the structure-activity relationship for chirality induction, transmission, and amplification.

View Article and Find Full Text PDF

Sucrose-Based Macrocycles: An Update.

Molecules

June 2025

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

Sucrose is by far the most abundant disaccharide found in nature, consisting of two simple hexose units: d-glucose and d-fructose. This exceptionally inexpensive and widely accessible raw material is produced in virtually limitless quantities. The vast majority is consumed in the food industry either in its native form-as commercial table sugar-or, to a lesser extent, as the basis for artificial sweeteners such as palatinose and sucralose.

View Article and Find Full Text PDF

Emerging mechanically interlocked cages.

Nat Rev Chem

August 2025

School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, China.

Mechanically interlocked molecules, including catenanes, rotaxanes and knots, are an intriguing class of synthetic targets with potential applications in molecular switches and machines. Although mechanically interlocked molecules are typically constructed using macrocyclic frameworks, the interlocking of two or more three-dimensional, shape-persistent cages remains relatively underexplored. Recent advances have accelerated the development of mechanically interlocked cages (MICs), which consist of interlocked three-dimensional molecular cages rather than macrocycles.

View Article and Find Full Text PDF