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Title: Rational Design of Stable Dianions by Functionalizing Polycyclic Aromatic Hydrocarbons

Abstract

Using density functional theory, we have carried out a systematic study of the stability and electronic properties of neutral and multiply charged molecules BnC10-nX8 (n=0, 1, 2; X=H, F, CN). Our main objective is to explore if the replacements of core C atoms and/or H atoms in naphthalene (C10H8) can enhance the stability of their dianions. Indeed, we find that the dianions of BnC10-n(CN)8 are more stable than their monoanions with energies of 0.61 eV, 0.57 eV, and 1.97 eV for n=0, 1, 2, respectively. In addition, polycyclic aromatic hydrocarbons become stable as dianions only when H atoms are substituted by more electronegative species. Thus, a rational design approach by tailoring composition and ligands can lead to a new class of organic molecules that are capable of carrying multiple charges.

Authors:
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory, Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC).
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division; USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR) (SC-21)
OSTI Identifier:
1461656
Grant/Contract Number:  
FG02-96ER45579; AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
ChemPhysChem
Additional Journal Information:
Journal Volume: 18; Journal Issue: 14; Journal ID: ISSN 1439-4235
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English

Citation Formats

None, None. Rational Design of Stable Dianions by Functionalizing Polycyclic Aromatic Hydrocarbons. United States: N. p., 2017. Web. doi:10.1002/cphc.201700346.
None, None. Rational Design of Stable Dianions by Functionalizing Polycyclic Aromatic Hydrocarbons. United States. doi:10.1002/cphc.201700346.
None, None. Mon . "Rational Design of Stable Dianions by Functionalizing Polycyclic Aromatic Hydrocarbons". United States. doi:10.1002/cphc.201700346. https://www.osti.gov/servlets/purl/1461656.
@article{osti_1461656,
title = {Rational Design of Stable Dianions by Functionalizing Polycyclic Aromatic Hydrocarbons},
author = {None, None},
abstractNote = {Using density functional theory, we have carried out a systematic study of the stability and electronic properties of neutral and multiply charged molecules BnC10-nX8 (n=0, 1, 2; X=H, F, CN). Our main objective is to explore if the replacements of core C atoms and/or H atoms in naphthalene (C10H8) can enhance the stability of their dianions. Indeed, we find that the dianions of BnC10-n(CN)8 are more stable than their monoanions with energies of 0.61 eV, 0.57 eV, and 1.97 eV for n=0, 1, 2, respectively. In addition, polycyclic aromatic hydrocarbons become stable as dianions only when H atoms are substituted by more electronegative species. Thus, a rational design approach by tailoring composition and ligands can lead to a new class of organic molecules that are capable of carrying multiple charges.},
doi = {10.1002/cphc.201700346},
journal = {ChemPhysChem},
number = 14,
volume = 18,
place = {United States},
year = {2017},
month = {5}
}

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Works referenced in this record:

Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993

  • Becke, Axel D.
  • The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
  • DOI: 10.1063/1.464913