Scalable Orbital Tuning of the 1,3-Diphosphacyclobutane-2,4-diyl Unit of Singlet Biradicaloid
The phosphino groups in 1,3-diphosphacyclobutane-2,4-diyl in the singlet biradicaloid play important roles in determining the physicochemical characteristics of the particular open-shell phosphorus heterocycles. Herein, we demonstrate that the introduction of para-substituted phenyl groups to the ph...
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| Published in | Journal of organic chemistry Vol. 85; no. 22; pp. 14384 - 14390 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
20.11.2020
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-3263 1520-6904 1520-6904 |
| DOI | 10.1021/acs.joc.0c00512 |
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| Abstract | The phosphino groups in 1,3-diphosphacyclobutane-2,4-diyl in the singlet biradicaloid play important roles in determining the physicochemical characteristics of the particular open-shell phosphorus heterocycles. Herein, we demonstrate that the introduction of para-substituted phenyl groups to the phosphorus atom induces useful photoabsorption and redox characteristics, as confirmed by the Hammett equation. These findings provided reliable methods for realizing desirable physicochemical properties of the open-shell singlet phosphorus heterocyclic chromophores based on programmed tuning of the molecular orbital energy levels of the particular open-shell singlet (non-Kekulé) heterocyclic unit. In addition, use of the thiophene substituent allowed confirmation of the orbital tuning by catenation of the P-heterocyclic units, with the >P–C4H2S–P< bridging component inducing splitting of the degenerate LUMO energy levels and destabilizing of the cationic species upon oxidation. |
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| AbstractList | The phosphino groups in 1,3-diphosphacyclobutane-2,4-diyl in the singlet biradicaloid play important roles in determining the physicochemical characteristics of the particular open-shell phosphorus heterocycles. Herein, we demonstrate that the introduction of para-substituted phenyl groups to the phosphorus atom induces useful photoabsorption and redox characteristics, as confirmed by the Hammett equation. These findings provided reliable methods for realizing desirable physicochemical properties of the open-shell singlet phosphorus heterocyclic chromophores based on programmed tuning of the molecular orbital energy levels of the particular open-shell singlet (non-Kekulé) heterocyclic unit. In addition, use of the thiophene substituent allowed confirmation of the orbital tuning by catenation of the P-heterocyclic units, with the >P–C₄H₂S–P< bridging component inducing splitting of the degenerate LUMO energy levels and destabilizing of the cationic species upon oxidation. The phosphino groups in 1,3-diphosphacyclobutane-2,4-diyl in the singlet biradicaloid play important roles in determining the physicochemical characteristics of the particular open-shell phosphorus heterocycles. Herein, we demonstrate that the introduction of para-substituted phenyl groups to the phosphorus atom induces useful photoabsorption and redox characteristics, as confirmed by the Hammett equation. These findings provided reliable methods for realizing desirable physicochemical properties of the open-shell singlet phosphorus heterocyclic chromophores based on programmed tuning of the molecular orbital energy levels of the particular open-shell singlet (non-Kekulé) heterocyclic unit. In addition, use of the thiophene substituent allowed confirmation of the orbital tuning by catenation of the P-heterocyclic units, with the >P-C4H2S-P< bridging component inducing splitting of the degenerate LUMO energy levels and destabilizing of the cationic species upon oxidation.The phosphino groups in 1,3-diphosphacyclobutane-2,4-diyl in the singlet biradicaloid play important roles in determining the physicochemical characteristics of the particular open-shell phosphorus heterocycles. Herein, we demonstrate that the introduction of para-substituted phenyl groups to the phosphorus atom induces useful photoabsorption and redox characteristics, as confirmed by the Hammett equation. These findings provided reliable methods for realizing desirable physicochemical properties of the open-shell singlet phosphorus heterocyclic chromophores based on programmed tuning of the molecular orbital energy levels of the particular open-shell singlet (non-Kekulé) heterocyclic unit. In addition, use of the thiophene substituent allowed confirmation of the orbital tuning by catenation of the P-heterocyclic units, with the >P-C4H2S-P< bridging component inducing splitting of the degenerate LUMO energy levels and destabilizing of the cationic species upon oxidation. The phosphino groups in 1,3-diphosphacyclobutane-2,4-diyl in the singlet biradicaloid play important roles in determining the physicochemical characteristics of the particular open-shell phosphorus heterocycles. Herein, we demonstrate that the introduction of para-substituted phenyl groups to the phosphorus atom induces useful photoabsorption and redox characteristics, as confirmed by the Hammett equation. These findings provided reliable methods for realizing desirable physicochemical properties of the open-shell singlet phosphorus heterocyclic chromophores based on programmed tuning of the molecular orbital energy levels of the particular open-shell singlet (non-Kekulé) heterocyclic unit. In addition, use of the thiophene substituent allowed confirmation of the orbital tuning by catenation of the P-heterocyclic units, with the >P–C4H2S–P< bridging component inducing splitting of the degenerate LUMO energy levels and destabilizing of the cationic species upon oxidation. The phosphino groups in 1,3-diphosphacyclobutane-2,4-diyl in the singlet biradicaloid play important roles in determining the physicochemical characteristics of the particular open-shell phosphorus heterocycles. Herein, we demonstrate that the introduction of para-substituted phenyl groups to the phosphorus atom induces useful photoabsorption and redox characteristics, as confirmed by the Hammett equation. These findings provided reliable methods for realizing desirable physicochemical properties of the open-shell singlet phosphorus heterocyclic chromophores based on programmed tuning of the molecular orbital energy levels of the particular open-shell singlet (non-Kekule) heterocyclic unit. In addition, use of the thiophene substituent allowed confirmation of the orbital tuning by catenation of the P-heterocyclic units, with the >P-C4H2S-P< bridging component inducing splitting of the degenerate LUMO energy levels and destabilizing of the cationic species upon oxidation. |
| Author | Ueta, Yasuhiro Ito, Shigekazu |
| AuthorAffiliation | School of Materials and Chemical Technology |
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| Keywords | CATENATION AIR-STABLE 1,3-DIPHOSPHACYCLOBUTANE-2,4-DIYLS DIRADICALS RING BONDS |
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| Snippet | The phosphino groups in 1,3-diphosphacyclobutane-2,4-diyl in the singlet biradicaloid play important roles in determining the physicochemical characteristics... |
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| SubjectTerms | Chemistry Chemistry, Organic energy equations organic chemistry oxidation phosphorus Physical Sciences Science & Technology thiophene |
| Title | Scalable Orbital Tuning of the 1,3-Diphosphacyclobutane-2,4-diyl Unit of Singlet Biradicaloid |
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