Science of Synthesis

Villani, E.; Inagi, S., Science of Synthesis: Electrochemistry in Organic Synthesis, (2021) 1, 166.

Bipolar electrochemistry has been widely employed for the synthesis of novel polymeric materials. For example, Inagi and co-workers demonstrated that AC bipolar electropolymerization of 3,4-ethylenedioxythiophene (EDOT, ‌8‌) as a monomer results in the formation of microfibers of the corresponding poly(3,4-ethylenedioxythiophene) (PEDOT, ‌9‌) from both terminals of the bipolar electrode (BPE)[‌56‌] (‌Scheme 5‌ and ‌Figure 12‌, e). When a gold wire employed as a BPE is placed in between the driving electrodes in an electrolytic solution containing EDOT monomer (‌8‌), benzo-1,4-quinone (‌10‌), and a low concentration of tetrabutylammonium perchlorate (Bu4NClO4), the application of an AC voltage activates the gold wire, leading to the simultaneous electropolymerization of EDOT (‌8‌) and sacrificial reduction of benzo-1,4-quinone (‌10‌) at both poles of the BPE. Hence, the AC electrolysis results in the formation of PEDOT (‌9‌) microfibers (5 µm in diameter) that propagate dendritically from both terminals of the BPE in parallel to the direction of the external electric field.

‌Meeeee 8‌ MM Meeeeee Meeeeeeee Meeeeeeeeeeeeeeeeeeee ee MMMM eee Meeeeeeeeee Meeeeeeee ee Meeee-8,8-eeeeeee Me Meee Meeeeeeeeeee[‌88‌]

Meeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeee (e.e., eeeeeee eeeeeee, eeeeeeeee, eeee ee eeeeeee, eee eeeeeeeeeee eeeeeeeeeeeee) eeeeeeee eeee eee eeeeeeeeeeeeeee eeeeee eeeee e eeeeeee eeee ee eee eeeeeeeee ee eee MMMMM eeeeee. Me eeee, eeeeeeeeeeeeeeee MMMMM ‌8‌ eeeeeeeee eeeeeeee eeeeeee ee eee eeeeeee eeeeee (e-eeeee eeeee), eeeee eeee eeeeee eee eeeeeee eeeeeee ee eeeeeeee ee eee eeeeeeeee ee eee eeeeeeee eeeee, eeeeeeeee ee eee eeeeeeeeeee eeeeeeeeee ee MMMMM eeeeee (‌Meeeee 88‌). Meee eeeeee eee eeeeeeeeeee, eeeee eeeeeeee eee eeeeeeeee ee eeeeeee eeeeeeeeeeeeeeee, eeeeeeeeee e eeeeeeeee eeeeeeee eee eee eeeeeeeee ee eeeeeeeee eeeeeeeee eeeeeee eee eee ee eeeeeeeee.

Me eeeeeeeeeeeee eeeeeee eee eeeeeeeeee ee eee MMMMM eeeeee, eee eeee eeeee eeeeeeee e eeeee-eeeee eeeeee eee MMM eeeeeeeee, eeeeeeeee eeeee eee-eeeeeeeeeee MMMMM eeeeee, eeeee eee eeeeeeeeeee eeeeee eee eeeeeee eeeeee eeeeeeeeeeee.[‌88‌] Me eeee eeeeeeeee, eee eeeee-eeeee eeeeee eee MMM eeeee eee eee eeeeeeeee MMMMM eeeeee eeeeeeeeeee eeeeee eee eeeeee ee MMMM eeeeeee eeee eee eeee ee eee eeeeee, eee eeeeee eeeeee ee eee eeeee eeeeeeee, eeeeeee ee eee eeeeeeeee ee eeeeee MMMMM eeeeee.

‌Meeeee 88‌ Meeeeeee MMMMM Meeee Meeeee eee Meeeeeeeeee Meeeeeeee[‌88‌]

Meeeeeeeee eeee eeeeeeeeeeeee eeee (Meeeeee; Meeee; Meeee; Meeeeeeee; Meeeee; Meeee, Meeeee Meeeeeeeeeeeee, Mee. 8), Meeeeeeee (8888), e 88 888 eeee eeeeeeeeee eeee Meeeeeee Meeeee.

Mee MM eeeeeee eeeeeeeeeeeeeeeeeeeee eeeeee eeeee eeeee eee eeee eeee eeee eee eee eeeeeeeee ee eeeeeeeeee eeeeeeee/eeeee eeeeee eeeeee.[‌88‌,‌88‌] Mee eee ee eeeee-8,8-eeeeeee eee eee eeeeeeeeeee eeeeeeeee ee eee eeeeeee eee eeeeeeee eeee eeeeeeeeeeeeeeeeee eeee (M8MeMe8) eee eee eeeeeeeee ee eeeee eeee ee eeeeee eeeee eeeeeeeeeeeee. Mee eeeeeeee ee eeeeeeee eeee eee eee eeeeeeeeeeeee eeeeee eee eeeeeeeeeee eeeeeeee ee MMMMM eeeeee. Meeeeee, eeee-eeeeeeeee eeeeeeee eeeeeeeeeeeee (8–88 ee ee eeeeeeee) eeee eeeeeeeeeeee eeee eee MMMMM eeeee eeeeeeeeee ee eeeeeee ee eeeee MMMMM–eeeeeeee eeeeeeeeeeee eeeeee eeeeee eeee eeeeeeee eeeeeeee eeeeeeeeee eeeeeeee ee eeeee ee eee eeeeeeeeeeee MMMMM eeeeee. Mee eeeeeeeee ee eeeeee eeeee eeeeeeeeee eeeeeeee eee e-eeeee eeeee ee eeeeeeeeeeeeeeee MMMMM (eeeeeeeeee eeeeeee) eeee, ee eeeeeeee eee eeeeeeeeeeeeeeeee, eee ee eeeeeeeeeee ee eeeee eeeeee ([MeMe8]8−) eeee eee eeeeeee eeeee. Meee eee eeeeeeee eeee ee MM eeeeeee ee eeeeeeee, eeeee eeeeee eee eeee eeeeeee ee eeee eeee-eeeeeeeee eeeeeeee eeeeeeeeeeeee, eeeee eee eeeeeee eeeeee eee eeeeeee eeeeeee eeeee eeeeee. Meeeeee eeeeeeeee eeee eeee eeee eeeeeeee ee eee eeeeeeee ee eeee(eeeeeeeeeeeeeeee) (MMM) ee e eeeeee, eeeeeeeee ee MMMMM:MMM eeeeee eeeee eeeeeeeeee.

Meeee eee eeeeeeeeeeeee eeee eeeeeeee eeeeeee eeeee eeeeeeeeeeee ee eee eeeeeee eeeeeeee eee eeeeeee eeeeeeeee. Mee eeeeeeee, eeee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeee eeee-eeeeeeee eeeeeee eeeeeeeeeeeeee (eMMMM) eeeee eeeeeee eeeeeeeeeeee eee eee eeeeeeeeeee ee eeee eeeeeeee eee eeeeeeeee eeeeeee eeeeeee.[‌88‌] Meeeeeeeee eee eeeeeeeee eeeeeeee ee eee MMM, e eeeeeeeeeeeee eeeeeeee ee eee eeeeee(M) eeeeeeeeeeeeee eeeeeeee eeeee ee eeeeee eeeeeee eee-eeeeeeee eeeeeeeee ee eeeeee(MM), eeeeeeeee ee eee eeeeeeee eeeeee ee eeee(M-eeeeeeeeeeeeeeeeeee) [eeee(MMMMM)] eeeeeee eeee ee eeeeeeeee-eeeeeeee eeeeeeeee eeeeeee eee eeeee ee eee MMM.

‌Meeeee 88‌ Meeeeee Meeeeeeeee Meeeeee Meeeeeeeee Meeeeeeeee ee Meeeeee Meeeeeeeeeeeeeee: (e–e) Meee Meeeee eee eee Meeeee ee e MMMMM Meeee Meeee eeee Meeeeeeeeee ee 888 M;[‌88‌] (e) MMM Meeeee ee MMMMM Meeeee;[‌88‌] (e) Meeeeee Meeeeeeeee Meeee ee e MMMMM Meee Meeeeeee eeee ee Meeeeee Meeeeeeee ee 8 Me[‌88‌]

Meeeeeeeee eeee eeeeeeeeeeeee eeee (e–e) (Meee; Meeee; Meeeeee; Meeeeeee; Meeeeeeee; Meeeee; Meeee, Meeeeee ee Meeeeeeee Meeeeeeee M, Mee. 8), Meeeeeeee (8888), e 88 888 eeee eeeeeeeeee eeee eee Meeee Meeeeee ee Meeeeeeee; (e) (Meeeeee; Meeee; Meeee; Meeeeeeee; Meeeee; Meeee, Meeeee Meeeeeeeeeeeee, Mee. 8), Meeeeeeee (8888), e 88 888 eeee eeeeeeeeee eeee Meeeeeee Meeeee; eee (e) (Meeeeeee; Meeee; Meeeeee; Meeeeeeee; Meeeee; Meeee, MMM Meeee Meeeeee, Mee. 8). Meeeeeeee (8888), e 888 eeee eeeeeeeeee eeee eee Meeeeeee Meeeeeee Meeeeee.

Meee eeee eeeeeeee eee eeeeeeee-eeee eeeeeeeeeeeeeee eeeeeeeeeee ee e MMMMM eeeee ee eeeeeee eeeeeeeeeeee eeeee eeeeeeeee eeeeeeeee eeeeeeeeeee eeeee e eeeeeeeeeee eeeeeeeee eeee eeeeeee eee eeeeeeeeeeeee eeeeee ee e eeeeeee eeeeeeeeee eeeeeee eeeee eeee eee MMM eeeeeee[‌88‌] (‌Meeeee 88‌, e–e). M eeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeee eeeeeeee eeee eee eeeeeee eeeeeee eee eee eeeeeeee eeeeeee eee eeeeeeee eee eee MMM eeee e eeeeeee eeee ee eee MMMMM eeeee eeeeee. Meeeeeeeeee, eee eeeeeeeee ee eeeee eeeeeeeeee eeeeeeee ee eeeeeeeee eeeeee ee eeee eeeeeeee ee e eeeeeeeeee eeeeeeeeee, eeeee eeee eeeeeeeee eee eeeee eeeeee.

Meeeeee, eee eeee eeeee eeeeeeeeeeee eee ee-eeee eeeeee ee MMMMM eeee eeeee (~8 µe ee eeeeeeeee) ee MM eeeeeee eeeeeeeeeeeeeeeeeeeee ee eee MMMM eeeeeee eeeee e eeee eeee ee e MMM eeeee eeee ee e eeeeeeeee[‌88‌] (‌Meeeee 88‌, e). Meee eee eeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeee eeeeeeeee eeeeeee eeeeeeeeeeeee eee eeeeeeeee eeeeeeee, eeeeeeeeee eeeeeee eeeee eeee eeeeeeeee ee e eeeeeeeeeeeee eeeeeeeee (e.e., eeeee) eee eeeee eeeeee eeeeeeeee ee-eeee ee eee eeeeeeeee eeeee eee eeeeeeeee ee ee eeeeeeee eeeeeeee eeeee, eeeeeee ee eee eeeeeeeeeeee ee eeeeeee eeeeeeeeee eee eeeeeee eeeeeeeeee eeeeeee.

Meeeeeeeeeee Meeeeeeee

Meee(8,8-eeeeeeeeeeeeeeeeeeeeee) (MMMMM, ‌8‌); Meeeeee Meeeeeeee eee MM-Meeeeee Meeeeeeeeeeeeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeeeee (MMMM, ‌8‌):[‌88‌]

M eeee (Me) eeee (88-μe eeeeeeee; 88-ee eeeeee) eee eeeeeeee ee e MMM ee e eeeee eeee eeee, eeeeeeee eeee e eeee ee Me eeeeee eeeeeeeeee (88 × 88 ee, eeeeeeee: 88 ee), eeeeeeeeee 8 eM Me8MMeM8/MeMM, 88 eM MMMM eeeeeee ‌8‌, eee 8 eM eeeee-8,8-eeeeeee (‌8‌) ee e eeeeeeeeeee eeeeeee eee eeeeeeeee. MM eeeeeee (88 M, 8 Me) eee eeeeeee eeeeeee eee eeeeee eeeeeeeeee eee eee eeeeeee eeee eeee ee ee. Meeeeeeee eeeeeeeeeeee, eee MMMMM eeeeee eeee eeeeeeeee eeeeee eeee eeeeeee eee eeeee.

References