English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
 
 
DownloadE-Mail
 Local TagsRelease HistoryDetailsSummary
  Mechanical reversibility of strain-promoted azide–alkyne cycloaddition reactions

Jacobs, M. J., Schneider, G., & Blank, K. (2016). Mechanical reversibility of strain-promoted azide–alkyne cycloaddition reactions. Angewandte Chemie International Edition, 55(8), 2899-2902. doi:10.1002/anie.201510299.

Item is

 

show all hide all

Basic

show hide
Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0029-7D21-6 Version Permalink: https://hdl.handle.net/21.11116/0000-0007-E7B3-A
Genre: Journal Article
Other : Mechanische Reversibilität der spannungskatalysierten Azid-Alkin-Cycloaddition

Files

show Files
hide Files
:
2247182.pdf (Publisher version), 897KB
 
File Permalink:
-
Name:
2247182.pdf
Description:
-
OA-Status:
Visibility:
Restricted (Max Planck Institute of Colloids and Interfaces, MTKG; )
MIME-Type / Checksum:
application/pdf
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-
:
2247182_supp.pdf (Supplementary material), 3MB
 
File Permalink:
-
Name:
2247182_supp.pdf
Description:
-
OA-Status:
Visibility:
Restricted (Max Planck Institute of Colloids and Interfaces, MTKG; )
MIME-Type / Checksum:
application/pdf
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-
:
Article_de.pdf (Publisher version), 1007KB
 
File Permalink:
-
Name:
Article_de.pdf
Description:
-
OA-Status:
Visibility:
Restricted (Max Planck Institute of Colloids and Interfaces, MTKG; )
MIME-Type / Checksum:
application/pdf
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-

Locators

show

Creators

show
hide
 Creators:
Jacobs, Monique J., Author
Schneider, Guenter, Author
Blank, Kerstin1, Author           
Affiliations:
1Kerstin Blank, Mechano(bio)chemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_persistent22              

Content

show
hide
Free keywords: alkynes, click chemistry, cycloaddition, density functional theory, mechanochemistry
 Abstract: Mechanophores, that is, molecules that show a defined response to force, are crucial building blocks of mechanoresponsive materials. The possibility of mechanically induced cycloreversion for a series of triazoles formed via strain-promoted azide–alkyne cycloaddition reactions was investigated by density functional theory calculations, and these triazoles were compared to the 1,4- and 1,5-regioisomers formed in the reaction of an azide with a terminal alkyne. We show that cycloreversion is in principal possible and that the pulling geometry is the most important parameter that determines the probability of cycloreversion. We further compared triazole stability to the mechanical stability of polymers that are frequently used as force transducers in mechanochemical experiments and identified DIBAC (azadibenzylcyclooctyne) as a promising mechanophore for future applications.

Details

show
hide
Language(s):
 Dates: 2016-01-252016
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1002/anie.201510299
DOI: 10.1002/ange.201510299
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 55 (8) Sequence Number: - Start / End Page: 2899 - 2902 Identifier: ISSN: 1433-7851

Source 2

show
hide
Title: Angewandte Chemie
  Abbreviation : Angew. Chem.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 128 (8) Sequence Number: - Start / End Page: 2950 - 2953 Identifier: ISSN: 0044-8249