Journal
JOURNAL OF PHYSICAL CHEMISTRY A
Volume 122, Issue 14, Pages 3583-3593Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jpca.7b12519
Keywords
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Funding
- Juniorprofessorenprogramm - Ministry of Science, Research and the Arts Baden-Wurttemberg (MWK)
- German Funding Agency (Deutsche Forschungsgemeinschaft-DFG) [SFB 716]
- bwHPC initiative
- bwHPC-05 project through JUSTUS HPC facility at the University of Ulm
- Ministry of Science, Research and the Arts Baden-Wurttemberg (MWK)
- German Research Foundation (DFG)
- Ministry of Science, Research and the Arts Baden-Wurttemberg
- DFG
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The rational control of the electronic and optical properties of small functionalized diamond-like molecules, the diamondoids, is the focus of this work. Specifically, we investigate the single- and double- functionalization of the lower diamondoids, adamantane, diamantane, and triamantane with -NH2 and -SH groups and extend the study to N-heterocyclic carbene (NHC) functionalization. On the basis of electronic structure calculations, we predict a significant change in the optical properties of these functionalized diamondoids. Our computations reveal that -NH2 functionalized diamondoids show UV photoluminescence similar to ideal diamondoids while -SH substituted diamondoids hinder the UV photoluminescence due to the labile nature of the S-H bond in the first excited state. This study also unveils that the UV photoluminescence nature of -NH2 diamondoids is quenched upon additional functionalization with the -SH group. The double-functionalized derivative can, thus, serve as a sensitive probe for biomolecule binding and sensing environmental changes. The preserved intrinsic properties of the NHC and the ideal diamondoid in NHC-functionalized-diamondoids suggests its utilization in diamondoid-based self-assembled monolayers (SAM), whose UV-photoluminescent signal would be determined entirely by the functionalized diamondoids. Our study aims to pave the path for tuning the properties of diamondoids through a selective choice of the type and number of functional groups. This will aid the realization of optoelectronic devices involving, for example, large-area SAM layers or diamondoid-functionalized electrodes.
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