Synthesis of a Trivalent P-Chloro-Dithienophosphole and its Reactivity with Organometallic Reagents
| dc.contributor.author | Gaffen, Joshua | |
| dc.contributor.author | Wang, Zisu | |
| dc.contributor.author | Baumgartner, Thomas | |
| dc.date.accessioned | 2020-07-14T19:52:26Z | |
| dc.date.available | 2020-07-14T19:52:26Z | |
| dc.date.issued | 2019-03-25 | |
| dc.description.abstract | P-chloro-dithieno[3,2-b:2’,3’-d]phosphole was synthesized and isolated from the reaction of an aminophosphole and HCl. Developed to act as a common starting material for P-functionalized phospholes, the compound exhibits a surprising reactivitiy by generating dimeric biphospholes. Despite this apparent sensitivity, when reacting with organolithium and Grignard reagents, a series of differently P-functionalized dithieno[3,2-b:2’,3’-d]phospholes was accessible. Unexpectedly, organolithium reagents showed reduced reactivity with the chlorophosphole, limiting yields of the desired products due to the competing dimerization. Nonetheless, P- functionalized phospholes were isolated from reactions of the title compound with both Grignard and organolithium reagents in yields equivalent to, or higher, than by previous methods. A bithiophene- bridged bisphosphole system was also successfully synthesized without the necessity of generating a bis(dichlorophosphino) reagent. Finally, the isolated P-functionalized phospholes were analyzed for their photophysical properties. In general, these compounds are strong absorbers in the UV/visible range of the optical spectrum. The phospholes’ emissions were consistent with several previously reported, however, typically with low quantum yields. | en_US |
| dc.description.sponsorship | NSERC, CFI, CRC, Alberta Innovates - Technology Futures | en_US |
| dc.identifier.citation | Eur. J. Inorg. Chem. 2019, 1612–1620 | en_US |
| dc.identifier.uri | http://dx.doi.org/10.1002/ejic.201801229 | en_US |
| dc.identifier.uri | http://hdl.handle.net/10315/37637 | |
| dc.language.iso | en | en_US |
| dc.publisher | Wiley | en_US |
| dc.rights | Attribution-NonCommercial-NoDerivs 2.5 Canada | * |
| dc.rights.article | https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejic.201801229 | en_US |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/2.5/ca/ | * |
| dc.subject | Research Subject Categories::NATURAL SCIENCES | en_US |
| dc.subject | Phosphanes | en_US |
| dc.subject | Phosphorus heterocycles | en_US |
| dc.subject | Organolithium reagents | en_US |
| dc.subject | Grignard reaction | en_US |
| dc.subject | Dimerization | en_US |
| dc.title | Synthesis of a Trivalent P-Chloro-Dithienophosphole and its Reactivity with Organometallic Reagents | en_US |
| dc.type | Article | en_US |