Cyclopentadithiophene polymers synthesised via Suzuki-Miyaura polymerisation of MIDA boronate esters

Cyclopentadithiophene (CPDT), a Csp3-bridged bithiophene heteroaromatic unit, displays interesting properties when it is embedded in the repeating units of π-conjugated polymers, and they are applied in organic electronics devices. Common synthetic routes to CPDT-derived polymers rely on toxic methodologies whilst alternative non-toxic strategies such as the Suzuki-Miyaura reaction have been less studied. In this report we demonstrate that the use of a N-methyliminodiacetic acid (MIDA) boronate ester-derived CPDT monomer allows the efficient formation of poly(cyclopentadithiophene) homopolymer under Suzuki-Miyaura cross-coupling reaction conditions. Thus, the use of MIDA boronate esters might be extended to other organic units to design and construct a plethora of π-conjugated polymers.

meta-Selective C–H functionalisation of aryl boronic acids directed by a MIDA-derived boronate ester

An N-methyliminodiacetic acid derivative allows the meta-C–H functionalisation of boronic acids, acting simultaneously as a directing and protecting group.

Regioselective routes to orthogonally-substituted aromatic MIDA boronates

A series of tetrasubstituted aromatics has been synthesized, many of which are based on elaborated N-methyliminodiacetic acid (MIDA)-boronates.