p-Doping of graphene in hybrid materials with 3,10-diazapicenium dications

Roth AM, Schaub T, Meinhardt U, Thiel D, Storch J, Cirkva V, Jakubik P, Guldi DM, Kivala M (2017)

Publication Type: Journal article

Publication year: 2017

Journal

Chemical Science Royal Society of Chemistry

Book Volume: 8

Pages Range: 3494-3499

Journal Issue: 5

DOI: 10.1039/C7SC00533D

Abstract

N,N$\prime$-Didodecyl-substituted 3,10-diazapicenium salts featuring bromide and hexafluorophosphate counterions have been designed as novel dopants to realize individualized graphene sheets in a series of cutting edge experiments and to intrinsically stabilize them via p-doping. Importantly, electrochemical studies revealed two consecutive irreversible one-electron reductions of the N,N$\prime$-didodecyl-substituted 3,10-diazapicenium salts to yield the corresponding radical cation and neutral quinoidal species. Formation of both species was accompanied by characteristic changes in the absorption spectra. The 3,10-diazapicenium bromide was found to be a potent dopant to produce hybrid materials with exfoliated graphene. Microscopy based on AFM and TEM imaging and spectroscopy based on Raman probing corroborated that, upon drying, the hybrid material consists of few layer (5--8 layers) turbostratic graphene sheets that are p-doped. Our findings identify the newly synthesized N,N$\prime$-dialkylated 3,10-diazapicenium salts as highly promising candidates for the fabrication of functional graphene materials with tailored properties.

Authors with CRIS profile

Alexandra Marina Roth Lehrstuhl für Physikalische Chemie I Tobias Schaub Sonderforschungsbereich 953/3 Synthetische Kohlenstoffallotrope Ute Meinhardt Lehrstuhl für Organische Chemie I Dominik Thiel Lehrstuhl für Physikalische Chemie I Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I Milan Kivala Lehrstuhl für Organische Chemie I

Additional Organisation(s)

Exzellenz-Cluster Engineering of Advanced Materials

Involved external institutions

Academy of Sciences of the Czech Republic (ASCR) / Akademie věd České republiky (AVČR) CZ Czech Republic (CZ)

How to cite

APA:

Roth, A.M., Schaub, T., Meinhardt, U., Thiel, D., Storch, J., Cirkva, V.,... Kivala, M. (2017). p-Doping of graphene in hybrid materials with 3,10-diazapicenium dications. Chemical Science, 8(5), 3494-3499. https://dx.doi.org/10.1039/C7SC00533D

MLA:

Roth, Alexandra Marina, et al. "p-Doping of graphene in hybrid materials with 3,10-diazapicenium dications." Chemical Science 8.5 (2017): 3494-3499.

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