Abstract
Thienyl di-MIDA boronate esters are readily synthesized
by electrophilic C-H borylation producing bench stable crystalline
solids in good yield and excellent purity. Optimal conditions
for the slow release of the boronic acid using KOH as the base in
biphasic THF/water mixtures enables the thienyl MIDA boronate
esters to be extremely effective homo-bifunctionalized (AA-type)
monomers in Suzuki-Miyaura co-polymerizations with dibromoheteroarenes
(BB-type monomers). A single polymerization protocol
is applicable for the formation of five alternating thienyl copolymers
that are (or are close analogues of) state of the art materials
used in organic electronics. The five polymers were produced in
excellent yields and with high molecular weights comparable to
those produced using Stille co-polymerization protocols. Therefore
thienyl di-MIDA boronate esters represent bench stable / low toxicity
alternatives to highly toxic di-trimethylstannyl AA-type monomers
that are currently ubiquitous in the synthesis of these important
alternating copolymers.
by electrophilic C-H borylation producing bench stable crystalline
solids in good yield and excellent purity. Optimal conditions
for the slow release of the boronic acid using KOH as the base in
biphasic THF/water mixtures enables the thienyl MIDA boronate
esters to be extremely effective homo-bifunctionalized (AA-type)
monomers in Suzuki-Miyaura co-polymerizations with dibromoheteroarenes
(BB-type monomers). A single polymerization protocol
is applicable for the formation of five alternating thienyl copolymers
that are (or are close analogues of) state of the art materials
used in organic electronics. The five polymers were produced in
excellent yields and with high molecular weights comparable to
those produced using Stille co-polymerization protocols. Therefore
thienyl di-MIDA boronate esters represent bench stable / low toxicity
alternatives to highly toxic di-trimethylstannyl AA-type monomers
that are currently ubiquitous in the synthesis of these important
alternating copolymers.
| Original language | English |
|---|---|
| Pages (from-to) | 13361-13368 |
| Number of pages | 8 |
| Journal | Journal of the American Chemical Society |
| Volume | 138 |
| Issue number | 40 |
| Early online date | 16 Sept 2016 |
| DOIs | |
| Publication status | Published - 12 Oct 2016 |
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CCDC 1493979: Experimental Crystal Structure Determination
Ayuso Carrillo, J. (Creator), Turner, M. (Contributor) & Ingleson, M. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2016
DOI: 10.5517/ccdc.csd.cc1m4lw7, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m4lw7&sid=DataCite
Dataset
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CCDC 1493980: Experimental Crystal Structure Determination
Ayuso Carrillo, J. (Contributor), Turner, M. (Contributor) & Ingleson, M. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2016
DOI: 10.5517/ccdc.csd.cc1m4lx8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m4lx8&sid=DataCite
Dataset