Narcissistic self-sorting and enhanced luminescence via catenation in water

Chen, Q.; Ye, Lei; Wang, H.; Wu, Guangcheng; Xu, Weilin; Jiao, Tianyu; Pan, Yuanjiang; Zhang, Q.; Zhang, Y.-M.; Liu, Y.; Li, H.

doi:10.1016/j.mtchem.2021.100679

Cited by 9 publications

(6 citation statements)

References 70 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…33B ) of both 1 3 S 6 and 1 3 R 6 were recorded, showing mirror-like images. When 1 was combined with a racemic mixture of ( R , R )-CHDA and ( S , S )-CHDA in CDCl 3 , narcissistic self-sorting 71 – 73 occurred (Supplementary Fig. 17 ), yielding a racemic mixture of 1 3 S 6 and 1 3 R 6 as the major product.…”

Section: Resultsmentioning

confidence: 99%

The sharp structural switch of covalent cages mediated by subtle variation of directing groups

Chen

et al. 2023

Nat Commun

View full text Add to dashboard Cite

It is considered a more formidable task to precisely control the self-assembled products containing purely covalent components, due to a lack of intrinsic templates such as transition metals to suppress entropy loss during self-assembly. Here, we attempt to tackle this challenge by using directing groups. That is, the self-assembly products of condensing a 1:2 mixture of a tetraformyl and a biamine can be precisely controlled by slightly changing the substituent groups in the aldehyde precursor. This is because different directing groups provide hydrogen bonds with different modes to the adjacent imine units, so that the building blocks are endowed with totally different conformations. Each conformation favors the formation of a specific product that is thus produced selectively, including chiral and achiral cages. These results of using a specific directing group to favor a target product pave the way for accomplishing atom economy in synthesizing purely covalent molecules without relying on toxic transition metal templates.

show abstract

Section: Resultsmentioning

confidence: 99%

The sharp structural switch of covalent cages mediated by subtle variation of directing groups

Chen

et al. 2023

Nat Commun

View full text Add to dashboard Cite

show abstract

“…The dynamic nature of hydrazone also facilitates the occurrence of self-sorting. For example, when two formyl precursors F23 2+ , F24 2+ (Figure a) and a hydrazide precursor A13 were combined in water, only the homocatenanes 36 4+ and 37 4+ were self-assembled, without generating the heterocatenane bearing two different macrocycles . The occurrence of narcissistic self-sorting resulted from the fact that, when two identical rings were mechanically interlocked, both of their cavities could be almost completely occupied so that the hydrophobic driving force was maximized.…”

Section: Characterization Of the Self-assembled Productsmentioning

confidence: 99%

Self-Assembly via Condensation of Imine or Its N-Substituted Derivatives

Chen,

Tang,

Chen

et al. 2023

Acc. Chem. Res.

View full text Add to dashboard Cite

Conspectus Compared to traditionally used irreversible chemical reactions, dynamic covalent chemistry (DCC) including imine formation represents a more advanced technique in the preparation of molecules with complex structures and topologies, whose syntheses require the formation of many bonds. By allowing the occurrence of error checking and self-correcting, it is likely that the target molecules with high enough thermodynamic stability could be self-assembled in high or even quantitative yield. Two questions are raised herein. First, it becomes a central problem in self-assembly that how to endow a target product with high enough thermodynamic stability so that it can be produced as the major or the only product within the self-assembly library. Second, the reversible nature of dynamic bonds jeopardizes the intrinsic stability of the products. More specifically, the imine bond which represents the mostly used dynamic covalent bond, is apt to undergo hydrolysis in the presence of water. Developing new approaches to make imine more robust and compatible with water is thus of importance. In this account, we summarized the progress made in our group in the field of self-assembly based on CN bond formation. In organic solvent where an imine bond is relatively robust, we focus on studying how to enhance the thermodynamic stability of a target molecule by introducing intramolecular forces. These noncovalent interactions either release enthalpy to favor the formation of the target molecule or preorganize the building blocks into specific conformations that mimic the product, so that the entropy loss of the formation of the latter is thus suppressed. In water, which often leads to imine hydrolysis, we developed two strategies to enhance the water-compatibility. By taking advantage of multivalency, namely, multiple bonds are often more robust than a single bond, self-assembly via condensation of imine was performed successfully in water, a solvent that is considered as forbidden zone of imine. Another approach is to replace typical imine with its more robust and water compatible derivatives, namely, either hydrazone or oxime, whose CN bonds are generally less electrophilic compared to typical imine. With the water-compatible dynamic bonds in hand, a variety topological nontrivial molecules such as catenanes and knots was self-assembled successfully in aqueous media, driven by hydrophobic effect. When the self-assembled molecules in the form of rings and cages were designed for supramolecular purposes, water-compatibility endows a merit that allows the hosts to take advantage of hydrophobic effect to drive host–guest recognition, enabling various tasks to be accomplished, such as separation of guest isomers with similar physical properties, recognition of highly hydrated anions, as well as stabilization of guest dimers.

show abstract

“…Furthermore, it is worth noting that even the emergence of aggregation-induced emission enhancement (AIEE) in certain nanospheres formed through self-assembly of macrocyclic molecules [73] , or thermodynamic narcissistic self-sorting structure [74] because of the preference for homotypic macrocyclic over heterotypic counterparts due to the maximization of non-covalent interactions between components, can be attributed to the synergistic effect of intramolecular rotation and intramolecular vibration leading to the activation of luminescence.…”

Section: Formentioning

confidence: 99%

Aggregation-induced emission materials based on restriction of intramolecular vibration

Lau,

Yang,

et al. 2023

Preprint

View full text Add to dashboard Cite

Aggregation-induced emission (AIE) is a photophysical phenomenon wherein luminescent materials exhibit weak emission in solution but strong emission after aggregation. This phenomenon has garnered significant attention in the realm of multifunctional luminescent materials. Specifically, AIE molecules, which operate through the restriction of intramolecular vibration (RIV) mechanism, have emerged as a pivotal constituent of AIE materials, captivating the interest of both academia and industry. This review aims to present a comprehensive overview of recent advancements in the domain of RIV-type AIE and its associated areas. It encompasses a survey of the classifications, molecular design strategies, and mechanisms underlying RIV-type AIE molecules. Furthermore, the review delves into the prospects and challenges encountered in the realm. We hope this review can provide novel insights into the theory, materials, and applications in the field of biochemistry and organic photoelectric.

show abstract

Narcissistic self-sorting and enhanced luminescence via catenation in water

Cited by 9 publications

References 70 publications

The sharp structural switch of covalent cages mediated by subtle variation of directing groups

The sharp structural switch of covalent cages mediated by subtle variation of directing groups

Self-Assembly via Condensation of Imine or Its N-Substituted Derivatives

Aggregation-induced emission materials based on restriction of intramolecular vibration

Contact Info

Product

Resources

About