Related Experiment Video
Updated: Aug 19, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Tristannosumanene-based substituent-defined binding pockets: substituent-dependent fullerene recognition and
Xuexiang Li1, Yang Zhang1, Jia Li1
1School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an, 710072, Shaanxi Province, P. R. China. lixuexiang@nwpu.edu.cn.
None:
Exploiting heavy main-group centers to create three-dimensional binding environments in π-frameworks offers an underexplored strategy for controlling fullerene assembly and electronic function. Herein, we report the first isolable tristannosumanenes, obtained via a one-step multi-site tin insertion into a triphenylene precursor. Single-crystal analysis showed that the tetracoordinate tin centers arrange their exocyclic substituents alternately above and below the π-plane, generating substituent-defined binding pockets whose depth is shifting from 2.1 Å (methyl) to 4.3 Å (phenyl substitution). The methyl-substituted 2a binds C60 in solution with a high association constant (Ka = 6.40 × 105 M-1), whereas DFT calculations reveal that deeper pockets do not enhance intrinsic affinity (ΔE = -0.25 vs. +1.39 kcal mol-1). FP-TRMC measurements showed contrasting photoconductivity trends upon fullerene complexation-suppression for 2a⊃C60 and enhancement for 2b⊃C60-correlated with their divergent packing topologies (Pnma vs. P2/n). These results establish substituent engineering at tetracoordinate tin centers as a practical strategy for altering binding-pocket geometry, fullerene organization, and charge-transport behavior in heterasumanene-based π-systems.
Related Concept Videos
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Directing Effect of Substituents: meta-Directing Groups
Directing and Steric Effects in Disubstituted Benzene Derivatives
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous overlap of p...
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...

