Related Experiment Video
Updated: Jun 21, 2025

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
Published on: February 27, 2017
Synthesis, Characterization and Interconversion of p-Tolylsulfone-Functionalized Norbornadiene/Quadricyclane Couples
Daniel Krappmann1, Andreas Hirsch1
1Department Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger Straße 10, 91058, Erlangen, Germany.
Abstract:
We report the synthesis and characterization of library of new 2,3-disubstituted norbornadiene/quadricyclane couples. For the first time, the para-tolylsulfone moiety was employed as electron-withdrawing substituent in combination with a variety of different electron donors as counterparts. Comprehensive characterization was conducted for every interconversion couple. By comparison with structurally related molecules published before we established the tosyl moiety as suitable alternative to previously investigated ester functionalities by providing similar photophysical properties. The photo-induced interconversion behavior was investigated via UV/Vis- and NMR-spectroscopy. The UV/Vis experiments were carried out exclusively in acetonitrile, whereas several solvents were investigated in the NMR studies. A detailed description and comparison of the isomerization behavior is provided, while examining relevant optical properties like λmax and λonset. Thereby, an enhanced red-shift up to λmax=394 nm combined with an λonset value of 469 nm could be generated which is necessary for potential applications.
More Related Videos
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
09:22Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
Related Concept Videos
Thermal and Photochemical Electrocyclic Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Stability of Conjugated Dienes
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Preparation and Reactions of Sulfides