Open-Shell Singlet Character of Stable Derivatives of Nonacene, Hexacene and Teranthene

Journal Article · Sat Jan 01 00:00:00 EST 2011 · Organic Letters

DOI:https://doi.org/10.1021/ol201004u· OSTI ID:1024700

Gao, Xingfa ^[1]; Jiang, Deen ^[2]; Zhang, Prof. Shengbai ^[3]; Chen, Zhongfang ^[4]; Miller, Glen ^[5]; Hodgson, Jennifer ^[5]

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1. Institute for Molecular Science, Japan
2. ORNL
3. Rensselaer Polytechnic Institute (RPI)
4. University of Georgia, Athens, GA
5. University of New Hampshire

The electronic ground states of the recently synthesized stable nonacene derivatives (J. Am. Chem. Soc.2010, 132, 1261) are open-shell singlets with a polyradical nature instead of closed-shell singlets as originally assumed, according to the unrestricted broken spin-symmetry density functional theory (UBS-DFT) computations (at B3LYP/6-31G*). It is the bulky protecting groups, not the transfer from the open-shell singlet to closed-shell singlet ground state, that stabilizes these longest characterized acenes. Similar analyses also confirmed the open-shell singlet character of the hexacene and teranthene derivatives.

• Research Organization: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
• Sponsoring Organization: USDOE Office of Science (SC)
• DOE Contract Number: DE-AC05-00OR22725
• OSTI ID: 1024700
• Journal Information: Organic Letters, Vol. 13, Issue 13; ISSN 1523--7060
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
FUNCTIONALS
GROUND STATES
ORNL