Journalartikel

Synthesis and Functionalization of Isomeric Sesquihomodiamantenes


AutorenlisteFokin, Andrey A.; Bakhonsky, Vladyslav V.; Pashenko, Alexander E.; Bakhiiev, Emirali; Becker, Jonathan; Kunz, Simon; Schreiner, Peter R.

Jahr der Veröffentlichung2023

Seiten14172-14177

ZeitschriftThe Journal of Organic Chemistry

Bandnummer88

Heftnummer19

ISSN0022-3263

eISSN1520-6904

DOI Linkhttps://doi.org/10.1021/acs.joc.3c01043

VerlagAmerican Chemical Society


Abstract
anti- and syn-sesquihomodiamantenes (SDs) were prepared and structurally characterized. anti-SD and parent sesquihomoadamantene were CH-bond functionalized by utilizing a phase-transfer protocol. The density functional theory-computed ionization potentials of unsaturated diamondoid dimers correlate well with the experimental oxidation potentials obtained from cyclic voltammetry. Similar geometries ensue for both the reduced and ionized SD states, whose persistence is supported by the beta-hydrogen's spatial sheltering. This makes SDs promising building blocks for the construction of diamond materials with high stability and carrier mobility.



Zitierstile

Harvard-ZitierstilFokin, A., Bakhonsky, V., Pashenko, A., Bakhiiev, E., Becker, J., Kunz, S., et al. (2023) Synthesis and Functionalization of Isomeric Sesquihomodiamantenes, The Journal of Organic Chemistry, 88(19), pp. 14172-14177. https://doi.org/10.1021/acs.joc.3c01043

APA-ZitierstilFokin, A., Bakhonsky, V., Pashenko, A., Bakhiiev, E., Becker, J., Kunz, S., & Schreiner, P. (2023). Synthesis and Functionalization of Isomeric Sesquihomodiamantenes. The Journal of Organic Chemistry. 88(19), 14172-14177. https://doi.org/10.1021/acs.joc.3c01043



Schlagwörter


ADAMANTYLIDENEADAMANTANEBROMONIUMELECTRONPHOTOEMISSIONRADICAL CATIONS


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