The Electro-Inductive Effect

Abstract: 

The electro-inductive effect offers a novel approach to modulating the chemical properties of molecules without the need for labor-intensive synthesis of derivatives with varying functional groups. By transmitting voltage-induced charge polarization from an electrode to molecules covalently attached to its surface, this method mimics the inductive effect of functional groups. Proof-of-concept studies with self-assembled monolayers of thiols on gold electrodes have demonstrated the potential of this technique for reaction control. However, such demonstrations have so far been limited to single-molecule scales.

Recently, we demonstrated that the electro-inductive effect can fine-tune the catalytic behavior of arylsulfonic acid immobilized on porous carbon electrodes for Brønsted acid-catalyzed organic reactions at millimolar scales. Applying voltages between -0.9 V and +0.8 V relative to the open circuit voltage modulated the yield of acid-catalyzed esterification by a factor of ~3. Furthermore, in the intramolecular nucleophilic substitution of an alcohol bound to a chiral carbon, the stereochemical outcome of carbocyclization was altered by adjusting the applied voltage. These results establish the electro-inductive effect as a scalable alternative to functional group modification for controlling catalytic organic reactions at practically relevant scales.

20250313_대학원 세미나_백무현 교수.pdf