title: Functionalized nanodiamonds: triamantane and [121]tetramantane.
abstract: The selective functionalizations of the fundamental hydrogen-terminated nanodiamonds triamantane 1, as well as the most symmetrical representative of the tetramantanes (C(2h)-[121]tetramantane 2) were elaborated. Electrophilic reagents (Br2, HNO3) predominantly attack the medial C-H positions of the cages; bromination of 2 gave the medial 2-bromo derivative almost exclusively. Highly selective apical substitution in 1 and 2 is possible either under single-electron-transfer oxidations via hydrocarbon radical cations or through photoacetylation with diacetyl. The mono- and the bis-acetyl derivatives of 1 and 2 were converted through Bayer-Villiger oxidation and subsequent hydrolysis to the respective apical mono- and dihydroxy derivatives. This exceptional synthetic specificity facilitates the transformation of 2, and perhaps larger nanodiamond molecules, into functionalized building blocks needed for a wide range of applications such as nanotechnology.
authors.affiliation: Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany. prs@org.chimie.uni-giessen.de
authors.forename: Peter R
authors.initials: PR
authors.lastname: Schreiner
authors.forename: Natalie A
authors.initials: NA
authors.lastname: Fokina
authors.forename: Boryslav A
authors.initials: BA
authors.lastname: Tkachenko
authors.forename: Heike
authors.initials: H
authors.lastname: Hausmann
authors.forename: Michael
authors.initials: M
authors.lastname: Serafin
authors.forename: Jeremy E P
authors.initials: JE
authors.lastname: Dahl
authors.forename: Shenggao
authors.initials: S
authors.lastname: Liu
authors.forename: Robert M K
authors.initials: RM
authors.lastname: Carlson
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Fokin