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Inorganics 2017, 5(4), 91; https://doi.org/10.3390/inorganics5040091

The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity

1
Department of Chemistry—BMC, Uppsala University, Box 576, SE-751 23 Uppsala, Sweden
2
Department of Chemistry-Ångström Laboratory Uppsala University, Box 523, SE-751 20 Uppsala, Sweden
*
Author to whom correspondence should be addressed.
Received: 23 October 2017 / Revised: 8 December 2017 / Accepted: 11 December 2017 / Published: 15 December 2017
(This article belongs to the Special Issue Coordination Chemistry of Silicon)
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Abstract

Baird’s rule tells that the electron counts for aromaticity and antiaromaticity in the first ππ* triplet and singlet excited states (T1 and S1) are opposite to those in the ground state (S0). Our hypothesis is that a silacyclobutene (SCB) ring fused with a [4n]annulene will remain closed in the T1 state so as to retain T1 aromaticity of the annulene while it will ring-open when fused to a [4n + 2]annulene in order to alleviate T1 antiaromaticity. This feature should allow the SCB ring to function as an indicator for triplet state aromaticity. Quantum chemical calculations of energy and (anti)aromaticity changes along the reaction paths in the T1 state support our hypothesis. The SCB ring should indicate T1 aromaticity of [4n]annulenes by being photoinert except when fused to cyclobutadiene, where it ring-opens due to ring-strain relief. View Full-Text
Keywords: Baird’s rule; computational chemistry; excited state aromaticity; Photostability Baird’s rule; computational chemistry; excited state aromaticity; Photostability
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ayub, R.; Jorner, K.; Ottosson, H. The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity. Inorganics 2017, 5, 91.

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