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Carbon–nitrogen nanorings and nanoribbons: a theoretical approach for altering the ground states of cyclacenes and polyacenes

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Abstract

Carbon–nitrogen nanorings with formulae (CN)2n and in the form of [n]pyrazine cyclacenes appear either as closed-shell singlets (SCS) for n = 5, 10, and 12, or open-shell singlets (SOS) for n = 6, 7, 9, and 11 at restricted and unrestricted broken spin-symmetry density functional theory (DFT). All of their corresponding acyclic isomers, which are called [n]pyrazine polyacenes or nanoribbons, appear as SCS for n = 5–12. As a result, nitrogen substitutions alter the electronic ground state of cyclacenes and polyacenes and appear to increase their viability, which invites further experimental and theoretical realization and exploration.

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Acknowledgment

We thank Mr. M. Ghambarian from Tarbiat Modares University for his stimulating and helpful discussions.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14155-4838, Tehran, Iran

    M. Z. Kassaee, H. Aref Rad & S. Soleimani Amiri

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  1. M. Z. Kassaee
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  2. H. Aref Rad
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Correspondence to M. Z. Kassaee.

Electronic supplementary material

Below is the link to the electronic supplementary material, which contains Cartesian coordinates, absolute energies, energy differences between different electronic states, bond lengths, spin contaminations, molecular orbital diagrams, frontier molecular orbital of [6]pyrazine cyclacene and [5]pyrazine polyacene, NICS values of pyrazine nanorings for all calculated compounds at the B3LYP/6-31G* level.

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Kassaee, M.Z., Aref Rad, H. & Soleimani Amiri, S. Carbon–nitrogen nanorings and nanoribbons: a theoretical approach for altering the ground states of cyclacenes and polyacenes. Monatsh Chem 141, 1313–1319 (2010). https://doi.org/10.1007/s00706-010-0398-x

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