Related Experiment Video
Updated: May 21, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
A Modular Approach Toward BN-Embedded Terrylene Diimides
Kexiang Zhao1, Yu-Chun Xu1, Jing-Cai Zeng1
1Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, P.R. China.
Abstract:
This work presents the first example of heteroatoms embedded terrylene diimides (TDIs), which were synthesized from the BN-embedded imide building block in a modular manner. Through the control of the amount and orientations of the BN unit(s), the manipulation of dipole moments of the obtained BN-embedded terrylene diimides (BN-TDIs) was achieved, which in turn extended the fluorescence of BN-TDIs to near infrared region. The structures of BN-TDIs were established via single crystal X-ray diffractions. Stronger carbonyl-π interactions were observed for BN-TDIs in their crystal structures compared with that of TDI, which could be utilized in the construction of supramolecular architectures. The organic thin film transistors based on BN-TDIs were also fabricated. BN-TDI-S showcased higher electron mobilities than that of TDI, indicating the potential of BN-TDIs as promising n-type organic semiconductors.
More Related Videos
Related Concept Videos
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the ÃÂÃÂ electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion...

