The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity
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 s...
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| Format: | Article |
| Language: | English |
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MDPI AG
2017-12-01
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| Series: | Inorganics |
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| Online Access: | https://www.mdpi.com/2304-6740/5/4/91 |
| _version_ | 1817976811612536832 |
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| author | Rabia Ayub Kjell Jorner Henrik Ottosson |
| author_facet | Rabia Ayub Kjell Jorner Henrik Ottosson |
| author_sort | Rabia Ayub |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T22:08:35Z |
| format | Article |
| id | doaj.art-f4aae1bd41ac4c89a9536ca427868bb8 |
| institution | Directory Open Access Journal |
| issn | 2304-6740 |
| language | English |
| last_indexed | 2024-04-13T22:08:35Z |
| publishDate | 2017-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj.art-f4aae1bd41ac4c89a9536ca427868bb82022-12-22T02:27:52ZengMDPI AGInorganics2304-67402017-12-01549110.3390/inorganics5040091inorganics5040091The Silacyclobutene Ring: An Indicator of Triplet State Baird-AromaticityRabia Ayub0Kjell Jorner1Henrik Ottosson2Department of Chemistry—BMC, Uppsala University, Box 576, SE-751 23 Uppsala, SwedenDepartment of Chemistry—BMC, Uppsala University, Box 576, SE-751 23 Uppsala, SwedenDepartment of Chemistry—BMC, Uppsala University, Box 576, SE-751 23 Uppsala, SwedenBaird’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.https://www.mdpi.com/2304-6740/5/4/91Baird’s rulecomputational chemistryexcited state aromaticityPhotostability |
| spellingShingle | Rabia Ayub Kjell Jorner Henrik Ottosson The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity Inorganics Baird’s rule computational chemistry excited state aromaticity Photostability |
| title | The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity |
| title_full | The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity |
| title_fullStr | The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity |
| title_full_unstemmed | The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity |
| title_short | The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity |
| title_sort | silacyclobutene ring an indicator of triplet state baird aromaticity |
| topic | Baird’s rule computational chemistry excited state aromaticity Photostability |
| url | https://www.mdpi.com/2304-6740/5/4/91 |
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