A series of photoswitchable cyclopentadienone derivative dimers bearing bromo, thienyl, 4-(dimethylamino)phenyl, 3-pyridinyl, 4-nitrophenyl and cyano groups was designed and facilely synthesized. Photoswitching properties such as the photoconversions in the photostationary state (PSS), the thermal kinetics and thermal half-lives of photoisomers were systematically investigated. These photoswitches show high fatigue resistance and large photoconversions in the PSS. This work proves that the photoswitching properties of photoswitches based on cyclopentadienone dimers can be tuned by substitution groups and also pave the way to functionalize the cyclopentadienone derivative dimer-based photoswitch, which is important for its future applications.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.202100070 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Gated off-site radical injection: Bidirectional conductance modulation in single-molecule junctions.
Sci Adv
November 2024
School of Optoelectronic Science and Engineering, University of Electronic Science and Technology of China (UESTC), Chengdu 611731, P. R. China.
Uncovering the effects of radical injection into responsive organic molecules is a long-sought goal, and the single-molecule junctions provide a unique way to investigate molecular conductance evolution during the radical injection. We can modulate the main channel conductance by using electronic injection from off-site neutral radicals acting as gating terminals. Two families of cyclopentadienone derivatives were synthesized, featuring the inter-pyridyl main conductance channel and the inter-radical paths that are linear (FCF) or cross conjugated (PCP).
View Article and Find Full Text PDFSerendipitous synthesis of phenanthrene derivatives by exploiting electrocyclization during thermolysis of Diels-Alder intermediate dihydrodibenzothiophene-,-dioxides.
Chem Commun (Camb)
November 2024
Department of Organic Chemistry, School of Chemical Sciences, University of Madras Guindy Campus, Chennai 600 025, Tamil Nadu, India.
Article Synopsis
- The Diels-Alder reaction was performed using tetraaryl cyclopentadienones and benzo[]thiophene-,-dioxides in nitrobenzene under reflux conditions.
- This led to the creation of fused phenanthrene derivatives through a process that involved eliminating SO from an intermediate and undergoing a 6π-electrocyclization.
- The methodology proved effective for synthesizing various phenanthrene derivatives with yields ranging from good to moderate.
Di-Isatropolone C, a Spontaneous Isatropolone C Dimer Derivative with Autophagy Activity.
Molecules
March 2024
CAMS Key Laboratory of Synthetic Biology for Drug Innovation, NHC Key Laboratory of Biotechnology for Microbial Drugs, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
Article Synopsis
- Isatropolone C is a compound with a complex tricyclic structure derived from a specific microbial species and has been shown to dimerize into di-isatropolone C in methanol.
- The NMR analysis of di-isatropolone C reveals a new cyclopentane ring connecting two isatropolone C molecules and provides insights into the configuration of its chiral carbons using advanced quantum calculations.
- Both isatropolone C and di-isatropolone C have been found to induce autophagy in HepG2 liver cancer cells, indicating their potential biological significance.
Design, Synthesis and Catalytic Activity of (Cyclopentadienone)iron Complexes Containing a Stereogenic Plane and a Stereogenic Axis.
Chemistry
December 2023
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, via Valleggio, 11, 22100, Como, Italy.
Herein, we report the synthesis and characterization of several chiral (cyclopentadienone)iron complexes (CICs) featuring either two (R)-BINOL-derived stereoaxes or a combination of one (R)-BINOL-derived stereoaxis and a stereogenic plane. The stereoplane-containing CICs were obtained as epimer mixtures, which were separated by flash column chromatography and assigned an absolute configuration based on XRD analysis, NMR and order of elution. The library was tested in the asymmetric hydrogenation of ketones showing good catalytic activity and a moderate stereoselectivity which, notably, is mostly imparted by the stereogenic plane.
View Article and Find Full Text PDFDesign, Synthesis, and Application of a Water-soluble Photocage for Aqueous Cyclopentadiene-based Diels-Alder Photoclick Chemistry in Hydrogels.
Angew Chem Int Ed Engl
April 2023
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA, 93106, USA.
Spatiotemporally functionalized hydrogels have exciting applications in tissue engineering, but their preparation often relies on radical-based strategies that can be deleterious in biological settings. Herein, the computationally guided design, synthesis, and application of a water-soluble cyclopentadienone-norbornadiene (CPD-NBD) adduct is disclosed as a diene photocage for radical-free Diels-Alder photopatterning. We show that this scalable CPD-NBD derivative is readily incorporated into hydrogel formulations, providing gels that can be patterned with dienophiles upon 365 nm uncaging of cyclopentadiene.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!