» Articles » PMID: 34163937

Towards Photoswitchable Quadruple Hydrogen Bonds a Reversible "photolocking" Strategy for Photocontrolled Self-assembly

Overview
Journal Chem Sci
Specialty Chemistry
Date 2021 Jun 24
PMID 34163937
Citations 3
Authors
Affiliations
Soon will be listed here.
Abstract

Developing new photoswitchable noncovalent interaction motifs with controllable bonding affinity is crucial for the construction of photoresponsive supramolecular systems and materials. Here we describe a unique "photolocking" strategy for realizing photoswitchable control of quadruple hydrogen-bonding interactions on the basis of modifying the ureidopyrimidinone (UPy) module with an -ester substituted azobenzene unit as the "photo-lock". Upon light irradiation, the obtained motif is capable of unlocking/locking the partial H-bonding sites of the UPy unit, leading to photoswitching between homo- and heteroquadruple hydrogen-bonded dimers, which has been further applied for the fabrication of novel tunable hydrogen bonded supramolecular systems. This "photolocking" strategy appears to be broadly applicable in the rational design and construction of other H-bonding motifs with sufficiently photoswitchable noncovalent interactions.

Citing Articles

Thiosemicarbazones as versatile photoswitches with light-controllable supramolecular activity.

Senturk B, Butschke B, Eisenreich F Chem Sci. 2025; 16(7):3130-3140.

PMID: 39829985 PMC: 11740093. DOI: 10.1039/d4sc08530b.


Visible-Light Driven Control Over Triply and Quadruply Hydrogen-Bonded Supramolecular Assemblies.

Hilton E, Jinks M, Burnett A, Warren N, Wilson A Chemistry. 2024; 30(20):e202304033.

PMID: 38190370 PMC: 11497329. DOI: 10.1002/chem.202304033.


Urea-Functionalized Heterocycles: Structure, Hydrogen Bonding and Applications.

Keszei S, Varadi M, Skoda-Foldes R Molecules. 2023; 28(23).

PMID: 38067487 PMC: 10708335. DOI: 10.3390/molecules28237757.


Visible-Light Switching of Metallosupramolecular Assemblies.

Kennedy A, DiNardi R, Fillbrook L, Donald W, Beves J Chemistry. 2022; 28(16):e202104461.

PMID: 35102616 PMC: 9302685. DOI: 10.1002/chem.202104461.

References
1.
Li S, Xiao T, Xia W, Ding X, Yu Y, Jiang J . New light on the ring-chain equilibrium of a hydrogen-bonded supramolecular polymer based on a photochromic dithienylethene unit and its energy-transfer properties as a storage material. Chemistry. 2011; 17(38):10716-23. DOI: 10.1002/chem.201100691. View

2.
South C, Burd C, Weck M . Modular and dynamic functionalization of polymeric scaffolds. Acc Chem Res. 2007; 40(1):63-74. DOI: 10.1021/ar0500160. View

3.
Zhao X, Wang X, Jiang X, Chen Y, Li Z, Chen G . Hydrazide-based quadruply hydrogen-bonded heterodimers. Structure, assembling selectivity, and supramolecular substitution. J Am Chem Soc. 2003; 125(49):15128-39. DOI: 10.1021/ja037312x. View

4.
Pochorovski I, Wang H, Feldblyum J, Zhang X, Antaris A, Bao Z . H-bonded supramolecular polymer for the selective dispersion and subsequent release of large-diameter semiconducting single-walled carbon nanotubes. J Am Chem Soc. 2015; 137(13):4328-31. DOI: 10.1021/jacs.5b01704. View

5.
de Greef T, Nieuwenhuizen M, Sijbesma R, Meijer E . Competitive intramolecular hydrogen bonding in oligo(ethylene oxide) substituted quadruple hydrogen bonded systems. J Org Chem. 2010; 75(3):598-610. DOI: 10.1021/jo902053t. View