Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 72, Pages 17481-17494Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002997
Keywords
boron clusters; carborane anions; liquid crystals; molecular structures; synthesis
Categories
Funding
- Foundation for Polish Science [TEAM/2016-3/24]
- NSF [DMR-1611250]
- National Science Center [OPUS 2015/17/B/ST5/02801]
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C(1)-vinylation of [closo-1-CB9H10](-) (A) and [closo-1-CB11H12](-) (B) with 4-benzyloxystyryl iodide followed by hydrogenation of the double bond and reductive deprotection of the phenol functionality led to C(1)-(4-hydroxyphenethyl) derivatives. The phenol functionality was protected as the acetate. The esters were then treated with PhI(OAc)(2) and the resulting isomers were separated kinetically (for derivatives of anion A) or by chromatography (for derivatives of anion B) giving the difunctionalized building blocks in overall yields of 9 % and 50 %, respectively. A similar series of reactions was performed starting with anions A and B and 4-methoxystyryl bromide and iodide. Significant differences in the reactivity of derivatives of the two carborane anions were rationalized with DFT computational results. Application of the difunctionalized carboranes as building blocks was demonstrated through preparation of two ionic liquid crystals. The extensive synthetic work is accompanied by single crystal XRD analysis of six derivatives.
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