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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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A Spatially Separated Germylene-Carbene Compound for Site-Selective Small-Molecule Activation.

Mingdong Zhong¹, Zheng Su¹, Xiaohui Jiang¹

¹Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, China.

Inorganic Chemistry

|July 7, 2025

Summary

A novel germylene-carbene compound was synthesized and demonstrated selective small-molecule activation. Reactivity depends on the reactant, with carbene sites activating electrophiles and germylene sites reacting with azides.

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Area of Science:

Organometallic Chemistry
Main Group Chemistry
Carbene and Germylene Chemistry

Background:

N-heterocyclic carbenes (NHCs) are versatile ligands and reactive species.
Germylenes, silicon analogs of carbenes, exhibit unique reactivity.
Compounds featuring both germylene and carbene moieties are rare, limiting studies on their combined reactivity.

Purpose of the Study:

To synthesize and characterize a spatially separated germylene-carbene compound.
To investigate the site-selective reactivity of this bifunctional molecule.
To explore its potential in small-molecule activation.

Main Methods:

Salt elimination reaction between an (amidinato)chlorogermylene and a deprotonated N-heterocyclic carbene.
Characterization using spectroscopic techniques and X-ray diffraction.
Reactions with various small molecules (isocyanates, isothiocyanates, BH3·SMe2, GeCl2·dioxane, S8, mesitylazide).
Density Functional Theory (DFT) calculations and Natural Population Analysis (NPA).

Main Results:

Successful synthesis and characterization of the germylene-carbene compound (1).
Demonstrated site-selective small-molecule activation: carbene center reacts with isocyanates, isothiocyanates, BH3·SMe2, and GeCl2·dioxane.
Germylene center selectively reacts with mesitylazide, forming imidogermane.
Two-fold addition products observed with S8 and BH3·SMe2 on both centers.
DFT calculations revealed electronic properties influencing reactivity: HOMO on carbene carbon, HOMO-2 on Ge lone pairs, LUMO on Ge 4p orbital.

Conclusions:

The synthesized germylene-carbene compound exhibits tunable, site-selective reactivity.
The electronic structure dictates preferential activation at either the carbene or germylene center.
This work expands the scope of bifunctional main group compounds and their applications in small-molecule activation.