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dc.contributor.authorIngleson, Michael James
dc.contributor.authorYuan, Kang
dc.contributor.authorKahan, Rachel J
dc.contributor.authorSi, Changfeng
dc.contributor.authorWilliams, Amy
dc.contributor.authorKirschner, Sven
dc.contributor.authorUzelac, Marina
dc.contributor.authorZysman-Colman, Eli
dc.contributor.authorIngleson, M. J.
dc.identifier.citationIngleson , M J , Yuan , K , Kahan , R J , Si , C , Williams , A , Kirschner , S , Uzelac , M , Zysman-Colman , E & Ingleson , M J 2020 , ' The synthesis of brominated-boron-doped PAHs by alkyne 1,1-bromoboration : mechanistic and functionalisation studies ' , Chemical Science , vol. 11 , no. 12 , pp. 3258-3267 .
dc.identifier.otherBibtex: C9SC05404A
dc.identifier.otherORCID: /0000-0001-7183-6022/work/70234010
dc.descriptionThe research leading to these results has received funding from the European Research Council under the Horizon 2020 Research and Innovation Program (Grant no. 769599), the Leverhulme Trust (RPG-2014-340) and the EPSRC (EP/P010482/1). C. Si thanks the China Scholarship Council (201806890001).en
dc.description.abstractThe synthesis of a range of brominated-Bn-containing (n = 1, 2) polycyclic aromatic hydrocarbons (PAHs) is achieved simply by reacting BBr3 with appropriately substituted alkynes via a bromoboration/electrophilic C-H borylation sequence. The brominated-Bn-PAHs were isolated as either the borinic acid or B-mesityl-protected derivatives, with the latter having extremely deep LUMOs for the B2-doped PAHs (with one example having a reduction potential of E1/2 = -0.96 V versus Fc+/Fc, Fc = ferrocene). Mechanistic studies revealed the reaction sequence proceeds by initial alkyne 1,1-bromoboration. 1,1-bromoboration also was applied to access a number of unprecedented 1-bromo-2,2-diaryl substituted vinylboronate esters direct from internal alkynes. Bromoboration/C-H borylation installs useful C-Br units onto the Bn-PAHs, which were utilised in Negishi coupling reactions, including for the installation of two triarylamine donor (D) groups onto a B2-PAH. The resultant D-A-D molecule has a low optical gap with an absorption onset at 750 nm and emission centered at 810 nm in the solid state.
dc.relation.ispartofChemical Scienceen
dc.subjectQD Chemistryen
dc.titleThe synthesis of brominated-boron-doped PAHs by alkyne 1,1-bromoboration : mechanistic and functionalisation studiesen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.description.statusPeer revieweden

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