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Insulated π-Conjugated Azido Scaffolds for Stepwise Functionalization via Huisgen Cycloaddition on Metal Oxide Surfaces.
Small
November 2024
Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1, Komaba, Meguro-ku, Tokyo, 153-8902, Japan.
In organic-inorganic hybrid devices, fine interfacial controls by organic components directly affect the device performance. However, fabrication of uniformed interfaces using π-conjugated molecules remains challenging due to facile aggregation by their strong π-π interaction. In this report, a π-conjugated scaffold insulated by covalently linked permethylated α-cyclodextrin moiety with an azido group is synthesized for surface Huisgen cycloaddition on metal oxides.
View Article and Find Full Text PDF[4+1] cyclization of α-diazo esters and mesoionic N-heterocyclic olefins.
Chem Commun (Camb)
April 2023
Davenport Chemical Research Laboratories Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Prompted by the recent stepwise mechanistic proposal for the Huisgen [3+2] cycloaddition reaction between enamine and α-diazo ester, where the nucleophilic addition of the enamine carbon onto the terminal nitrogen of diazo ester is crucial, we examined the possible use of N-heterocyclic olefins (NHOs) as highly electron-rich dipolarophiles in these reactions. The mesoionic NHOs derived from 1,2,3-triazoles undergo fast [4+1] cycloaddition to give 3-(triazolium-4-yl)-(3)-pyrazol-4-olates at room temperature. The reaction mechanism has been explored through experimental and DFT computational studies.
View Article and Find Full Text PDFOne-Bond-Nucleophilicity and -Electrophilicity Parameters: An Efficient Ordering System for 1,3-Dipolar Cycloadditions.
J Am Chem Soc
April 2023
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany.
Diazoalkanes are ambiphilic 1,3-dipoles that undergo fast Huisgen cycloadditions with both electron-rich and electron-poor dipolarophiles but react slowly with alkenes of low polarity. Frontier molecular orbital (FMO) theory considering the 3-center-4-electron π-system of the propargyl fragment of diazoalkanes is commonly applied to rationalize these reactivity trends. However, we recently found that a change in the mechanism from cycloadditions to azo couplings takes place due to the existence of a previously overlooked lower-lying unoccupied molecular orbital.
View Article and Find Full Text PDFPrecise Stepwise Synthesis of Donor-Acceptor Conjugated Polymer Brushes Grafted from Surfaces.
Int J Mol Sci
May 2022
Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387 Kraków, Poland.
Donor-acceptor (D-A) conjugated polymers are promising materials in optoelectronic applications, especially those forming ordered thin films. The processability of such conjugated macromolecules is typically enhanced by introducing bulky side chains, but it may affect their ordering and/or photophysical properties of the films. We show here the synthesis of surface-grafted D-A polymer brushes using alternating attachment of tailored monomers serving as electron donors (D) and acceptors (A) via coupling reactions.
View Article and Find Full Text PDFSequence-Defined Macrocycles for Understanding and Controlling the Build-up of Hierarchical Order in Self-Assembled 2D Arrays.
J Am Chem Soc
November 2019
Molecular Materials Design Laboratory, Department of Chemistry , Indiana University, 800 East Kirkwood Avenue , Bloomington , Indiana 47405 , United States.
Anfinsen's dogma that sequence dictates structure is fundamental to understanding the activity and assembly of proteins. This idea has been applied to all manner of oligomers but not to the behavior of cyclic oligomers, aka macrocycles. We do this here by providing the first proofs that sequence controls the hierarchical assembly of nonbiological macrocycles, in this case, at graphite surfaces.
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