Synthesis and electrochemical properties of a new class of boron-containing n-type conjugated polymers

Doping the Backbone of π‐Conjugated Polymers with Tricoordinate Boron: Synthetic Strategies and Emerging Applications

“…Nonetheless, it reacted with pyridine to give a soluble, monomeric diadduct, and it brought about clean hydroboration of tert ‐butylacetylene or phenylacetylene, respectively . In combination with the 1,4‐diethynylbenzene derivatives 4 a,b , hydroboration polymerization occurred to give 5 a and 5 b . While the former was only poorly soluble, polymer 5 b , with the solubilizing hexyloxy side chains, showed good solubility in organic solvents .…”

“…For example, a poly(thienylborane) was obtained by a polycondensation‐postmodification sequence similar to the one shown in Scheme . Jia and co‐workers incorporated 9,10‐diboraanthracene units via B‐aryl linkages into conjugated polymers by the use of a Sn/B exchange procedure . A drawback of this method, however, is the pronounced toxicity of the organotin compounds involved.…”

“…The potential use of diboraanthracene‐containing polymers as n ‐type materials in organic photovoltaics was investigated by Jia and co‐workers . In a preliminary study, they performed photoluminescence quenching experiments on films of P3HT blended with a diboraanthracene‐based polymer spin‐coated on a silicon wafer (film thickness, d ≈1 μm).…”

Recent Advances in the Synthesis and Applications of Organoborane Polymers

“…We demonstrated more recently that reaction of distannyl species with arylboranes ArBX 2 or X(R)B-Ar-B(R)X (X ¼ Br, Cl) results in highly selective polymer formation under mild conditions via Sn-B exchange (23, Scheme 5b) [89][90][91][92][93]. Transition metal-catalyzed C-C coupling processes have also attracted increased attention.…”

Organometallic synthesis of n‐type π‐conjugated polymers with dopant cation trapping sites and stability of n‐doping state against air

“…π‐Conjugated polymers have attracted considerable attention due to their interesting chemical properties and practical applications because they can undergo a reductive (n‐type) or an oxidative (p‐type) doping that effectively converts them into conducting materials . However, there are considerably fewer reports on n‐type conductive polymers than on p‐type ones because of the difficulty associated with synthesizing n‐type π‐conjugated polymers and their low solubility in organic solvents 2–12. n‐Doping of π‐conjugated polymers is carried out by treating them with alkali metals such as sodium and potassium and subsequently applying to them an adequate potential so as to cause their electrochemical reduction , .…”