Catalytic Synthesis of Donor-Acceptor-Donor (D-A-D) and Donor-Acceptor-Acceptor (D-A-A) Pyrimidine-Ferrocenes via Acceptorless Dehydrogenative Coupling: Synthesis, Structures, and Electronic Communication

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dc.contributor.authorMondal, Rajarshi
dc.contributor.authorBraun, Jason
dc.contributor.authorSidhu, Baldeep K
dc.contributor.authorNevonen, Dustin
dc.contributor.authorNemykin, Victor
dc.contributor.authorHerbert, David E
dc.date.accessioned2021-10-22T17:54:06Z
dc.date.available2021-10-22T17:54:06Z
dc.date.issued2021-06-02
dc.date.submitted2021-10-15T20:54:49Zen_US
dc.description.abstractThe synthesis and full characterization of a series of ferrocene-decorated pyrimidines with donor-acceptor-donor (D-A-D) and donor-acceptor-acceptor (D-A-A) architectures are reported. The three novel compounds share a pyrimidine core and single ferrocenyl donor arm, with an additional substituent varied from donor ferrocene (1) to acceptor pyrenyl (2) to donor (4-diphenylamino)phenyl groups (3). The compounds could be easily constructed in acceptable yields in one-pot reactions via acceptorless dehydrogenative coupling reactions mediated by a ruthenium coordination complex supported by a simple bidentate P^N ligand. The solution and solid-state structures of the new pyrimidines are described along with photophysical and computational characterization. The lack of near IR (NIR) transitions upon single-electron oxidation of the compounds implies that the pyrimidinyl unit is less effective at mediating electronic communication compared with pyridine or pyrrole cores. Nevertheless, strong absorption in the far visible and NIR is observed upon formation of a dicationic species from 3 and is attributed to efficient charge transfer from the pyrimidine core to the oxidized donor units.en_US
dc.description.sponsorshipNatural Sciences and Engineering Research Council of Canada (RGPIN-2014-03733)en_US
dc.identifier.citationOrganometallics 2021, 40(11), 1765–1775en_US
dc.identifier.doi10.1021/acs.organomet.1c00232
dc.identifier.urihttp://hdl.handle.net/1993/36059
dc.language.isoengen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsopen accessen_US
dc.subjectOrganometallic Catalysisen_US
dc.titleCatalytic Synthesis of Donor-Acceptor-Donor (D-A-D) and Donor-Acceptor-Acceptor (D-A-A) Pyrimidine-Ferrocenes via Acceptorless Dehydrogenative Coupling: Synthesis, Structures, and Electronic Communicationen_US
dc.typePreprinten_US
local.author.affiliationFaculty of Scienceen_US
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