Anthracene as a Launchpad for a Phosphinidene Sulfide and for Generation of a Phosphorus–Sulfur Material Having the Composition P 2 S, a Vulcanized Red Phosphorus That Is Yellow

Anthracene as a Launchpad for a Phosphinidene Sulfide and for Generation of a Phosphorus–Sulfur Material Having the Composition P 2 S, a Vulcanized Red Phosphorus That Is Yellow. Transue, W., J., Nava, M., Terban, M., W., Yang, J., Greenberg, M., W., Wu, G., Foreman, E., S., Mustoe, C., L., Kennepohl, P., Owen, J., S., Billinge, S., J., L., Kulik, H., J., & Cummins, C., C. Journal of the American Chemical Society, 141(1):431-440, American Chemical Society, 1, 2019.

Paper

Website doi abstract bibtex 3 downloads

Thermolysis of a pair of dibenzo-7-phosphanorbornadiene compounds is shown to lead to differing behaviors: phosphinidene sulfide release and formation of amorphous P2S. These compounds, tBuP(S)A (1, A = C14H10 or anthracene; 59% isol. yield) and HP(S)A (2; 63%), are available through thionation of tBuPA and the new secondary phosphine HPA (5), which is prepared from Me2NPA in 50% yield by reaction with DIBAL-H. Phosphinidene sulfide [tBuP=S] transfer is shown to proceed efficiently from 1 to 1,3-dimethyl-2,3-butadiene to form Diels-Alder product 3 with a zero order dependence on diene. Platinum complex (Ph3P)2Pt(η2-tBuPS) (4, 47%) is also accessed from 1 and structurally characterized. In contrast, heating parent species 2 (3 h, 135 °C) under vacuum instead produces an insoluble and nonvolatile yellow residual material 6 of composition P2S that displays semiconductor properties with an optical band gap of 2.4 eV. The P2S material obtained in this manner from molecular precursor HP(S)A, shown by X-ray crys...

@article{
 title = {Anthracene as a Launchpad for a Phosphinidene Sulfide and for Generation of a Phosphorus–Sulfur Material Having the Composition P 2 S, a Vulcanized Red Phosphorus That Is Yellow},
 type = {article},
 year = {2019},
 pages = {431-440},
 volume = {141},
 websites = {http://pubs.acs.org/doi/10.1021/jacs.8b10775},
 month = {1},
 publisher = {American Chemical Society},
 day = {9},
 id = {fd714c41-09bb-3b53-aac2-8520ad81d239},
 created = {2018-12-15T01:00:19.202Z},
 accessed = {2018-12-14},
 file_attached = {true},
 profile_id = {8c5f55f8-b69e-30e2-981b-01f0d567bbfe},
 last_modified = {2020-04-22T14:44:12.700Z},
 read = {true},
 starred = {false},
 authored = {true},
 confirmed = {true},
 hidden = {false},
 private_publication = {false},
 abstract = {Thermolysis of a pair of dibenzo-7-phosphanorbornadiene compounds is shown to lead to differing behaviors: phosphinidene sulfide release and formation of amorphous P2S. These compounds, tBuP(S)A (1, A = C14H10 or anthracene; 59% isol. yield) and HP(S)A (2; 63%), are available through thionation of tBuPA and the new secondary phosphine HPA (5), which is prepared from Me2NPA in 50% yield by reaction with DIBAL-H. Phosphinidene sulfide [tBuP=S] transfer is shown to proceed efficiently from 1 to 1,3-dimethyl-2,3-butadiene to form Diels-Alder product 3 with a zero order dependence on diene. Platinum complex (Ph3P)2Pt(η2-tBuPS) (4, 47%) is also accessed from 1 and structurally characterized. In contrast, heating parent species 2 (3 h, 135 °C) under vacuum instead produces an insoluble and nonvolatile yellow residual material 6 of composition P2S that displays semiconductor properties with an optical band gap of 2.4 eV. The P2S material obtained in this manner from molecular precursor HP(S)A, shown by X-ray crys...},
 bibtype = {article},
 author = {Transue, Wesley J. and Nava, Matthew and Terban, Maxwell W. and Yang, Jing and Greenberg, Matthew W. and Wu, Gang and Foreman, Elizabeth S. and Mustoe, Chantal L. and Kennepohl, Pierre and Owen, Jonathan S. and Billinge, Simon J. L. and Kulik, Heather J. and Cummins, Christopher C.},
 doi = {10.1021/jacs.8b10775},
 journal = {Journal of the American Chemical Society},
 number = {1},
 keywords = {SSRL,X-ray Absorption Spectroscopy}
}

Downloads: 3

{"_id":"XtTCkbCkmMPr9BqHu","bibbaseid":"transue-nava-terban-yang-greenberg-wu-foreman-mustoe-etal-anthraceneasalaunchpadforaphosphinidenesulfideandforgenerationofaphosphorussulfurmaterialhavingthecompositionp2savulcanizedredphosphorusthatisyellow-2019","downloads":3,"creationDate":"2019-04-17T04:07:32.108Z","title":"Anthracene as a Launchpad for a Phosphinidene Sulfide and for Generation of a Phosphorus–Sulfur Material Having the Composition P 2 S, a Vulcanized Red Phosphorus That Is Yellow","author_short":["Transue, W., J.","Nava, M.","Terban, M., W.","Yang, J.","Greenberg, M., W.","Wu, G.","Foreman, E., S.","Mustoe, C., L.","Kennepohl, P.","Owen, J., S.","Billinge, S., J., L.","Kulik, H., J.","Cummins, C., C."],"year":2019,"bibtype":"article","biburl":"https://bibbase.org/service/mendeley/8c5f55f8-b69e-30e2-981b-01f0d567bbfe","bibdata":{"title":"Anthracene as a Launchpad for a Phosphinidene Sulfide and for Generation of a Phosphorus–Sulfur Material Having the Composition P 2 S, a Vulcanized Red Phosphorus That Is Yellow","type":"article","year":"2019","pages":"431-440","volume":"141","websites":"http://pubs.acs.org/doi/10.1021/jacs.8b10775","month":"1","publisher":"American Chemical Society","day":"9","id":"fd714c41-09bb-3b53-aac2-8520ad81d239","created":"2018-12-15T01:00:19.202Z","accessed":"2018-12-14","file_attached":"true","profile_id":"8c5f55f8-b69e-30e2-981b-01f0d567bbfe","last_modified":"2020-04-22T14:44:12.700Z","read":"true","starred":false,"authored":"true","confirmed":"true","hidden":false,"private_publication":false,"abstract":"Thermolysis of a pair of dibenzo-7-phosphanorbornadiene compounds is shown to lead to differing behaviors: phosphinidene sulfide release and formation of amorphous P2S. These compounds, tBuP(S)A (1, A = C14H10 or anthracene; 59% isol. yield) and HP(S)A (2; 63%), are available through thionation of tBuPA and the new secondary phosphine HPA (5), which is prepared from Me2NPA in 50% yield by reaction with DIBAL-H. Phosphinidene sulfide [tBuP=S] transfer is shown to proceed efficiently from 1 to 1,3-dimethyl-2,3-butadiene to form Diels-Alder product 3 with a zero order dependence on diene. Platinum complex (Ph3P)2Pt(η2-tBuPS) (4, 47%) is also accessed from 1 and structurally characterized. In contrast, heating parent species 2 (3 h, 135 °C) under vacuum instead produces an insoluble and nonvolatile yellow residual material 6 of composition P2S that displays semiconductor properties with an optical band gap of 2.4 eV. The P2S material obtained in this manner from molecular precursor HP(S)A, shown by X-ray crys...","bibtype":"article","author":"Transue, Wesley J. and Nava, Matthew and Terban, Maxwell W. and Yang, Jing and Greenberg, Matthew W. and Wu, Gang and Foreman, Elizabeth S. and Mustoe, Chantal L. and Kennepohl, Pierre and Owen, Jonathan S. and Billinge, Simon J. L. and Kulik, Heather J. and Cummins, Christopher C.","doi":"10.1021/jacs.8b10775","journal":"Journal of the American Chemical Society","number":"1","keywords":"SSRL,X-ray Absorption Spectroscopy","bibtex":"@article{\n title = {Anthracene as a Launchpad for a Phosphinidene Sulfide and for Generation of a Phosphorus–Sulfur Material Having the Composition P 2 S, a Vulcanized Red Phosphorus That Is Yellow},\n type = {article},\n year = {2019},\n pages = {431-440},\n volume = {141},\n websites = {http://pubs.acs.org/doi/10.1021/jacs.8b10775},\n month = {1},\n publisher = {American Chemical Society},\n day = {9},\n id = {fd714c41-09bb-3b53-aac2-8520ad81d239},\n created = {2018-12-15T01:00:19.202Z},\n accessed = {2018-12-14},\n file_attached = {true},\n profile_id = {8c5f55f8-b69e-30e2-981b-01f0d567bbfe},\n last_modified = {2020-04-22T14:44:12.700Z},\n read = {true},\n starred = {false},\n authored = {true},\n confirmed = {true},\n hidden = {false},\n private_publication = {false},\n abstract = {Thermolysis of a pair of dibenzo-7-phosphanorbornadiene compounds is shown to lead to differing behaviors: phosphinidene sulfide release and formation of amorphous P2S. These compounds, tBuP(S)A (1, A = C14H10 or anthracene; 59% isol. yield) and HP(S)A (2; 63%), are available through thionation of tBuPA and the new secondary phosphine HPA (5), which is prepared from Me2NPA in 50% yield by reaction with DIBAL-H. Phosphinidene sulfide [tBuP=S] transfer is shown to proceed efficiently from 1 to 1,3-dimethyl-2,3-butadiene to form Diels-Alder product 3 with a zero order dependence on diene. Platinum complex (Ph3P)2Pt(η2-tBuPS) (4, 47%) is also accessed from 1 and structurally characterized. In contrast, heating parent species 2 (3 h, 135 °C) under vacuum instead produces an insoluble and nonvolatile yellow residual material 6 of composition P2S that displays semiconductor properties with an optical band gap of 2.4 eV. The P2S material obtained in this manner from molecular precursor HP(S)A, shown by X-ray crys...},\n bibtype = {article},\n author = {Transue, Wesley J. and Nava, Matthew and Terban, Maxwell W. and Yang, Jing and Greenberg, Matthew W. and Wu, Gang and Foreman, Elizabeth S. and Mustoe, Chantal L. and Kennepohl, Pierre and Owen, Jonathan S. and Billinge, Simon J. L. and Kulik, Heather J. and Cummins, Christopher C.},\n doi = {10.1021/jacs.8b10775},\n journal = {Journal of the American Chemical Society},\n number = {1},\n keywords = {SSRL,X-ray Absorption Spectroscopy}\n}","author_short":["Transue, W., J.","Nava, M.","Terban, M., W.","Yang, J.","Greenberg, M., W.","Wu, G.","Foreman, E., S.","Mustoe, C., L.","Kennepohl, P.","Owen, J., S.","Billinge, S., J., L.","Kulik, H., J.","Cummins, C., C."],"urls":{"Paper":"https://bibbase.org/service/mendeley/8c5f55f8-b69e-30e2-981b-01f0d567bbfe/file/6a623453-e70c-8d03-6bd5-9f4b86e91b91/jacs8b10775.pdf.pdf","Website":"http://pubs.acs.org/doi/10.1021/jacs.8b10775"},"biburl":"https://bibbase.org/service/mendeley/8c5f55f8-b69e-30e2-981b-01f0d567bbfe","bibbaseid":"transue-nava-terban-yang-greenberg-wu-foreman-mustoe-etal-anthraceneasalaunchpadforaphosphinidenesulfideandforgenerationofaphosphorussulfurmaterialhavingthecompositionp2savulcanizedredphosphorusthatisyellow-2019","role":"author","keyword":["SSRL","X-ray Absorption Spectroscopy"],"metadata":{"authorlinks":{"kennepohl, p":"https://bibbase.org/service/mendeley/8c5f55f8-b69e-30e2-981b-01f0d567bbfe"}},"downloads":3,"html":""},"search_terms":["anthracene","launchpad","phosphinidene","sulfide","generation","phosphorus","sulfur","material","having","composition","vulcanized","red","phosphorus","yellow","transue","nava","terban","yang","greenberg","wu","foreman","mustoe","kennepohl","owen","billinge","kulik","cummins"],"keywords":["ssrl","x-ray absorption spectroscopy"],"authorIDs":["3iLerqnFcxCPMtJpn","4c6QnidJqyh8QxqkX","549f69158e3bca5f370014e6","5de7ed0bc8f9f6df010001e4","5de839c88cf0fbde0100006d","5deacdf2cd660bde01000195","5debd29aca1cdddf01000146","5df7dc76dc100cde010000ff","5e042bf8c51eb3de0100007b","5e07c8ccea5f0bdf010000cf","5e0dc56cc7ca67df01000115","5e0ec889b68da9de01000034","5e0f7abf99975cde0100009e","5e10afd9cfb06ddf0100006d","5e1177267da100de0100012f","5e13d054280ddede0100016e","5e164e4428f1c0de0100031d","5e1693f8da4561de0100001f","5e177475cf35a4de01000031","5e1a947969523cde01000099","5e257428f58a5cde010000f1","5e2882d967e11edf010000ac","5e28f4bc41639df301000044","5e2e93568d5204de0100007e","5e31e94fbba4d0de01000241","5e326d5e5633c9de010000a3","5e342fca41f782de0100012d","5e35488dba591ddf0100008c","5e3665ad4b25bbf2010000d2","5e382dc30691b8de010001ff","5e3c4312c798e0de01000034","5e46844d71278bde010000cc","5e4eb15264b624de010001a8","5e4f912b42a908de010000f4","5e4fbd2d2c51e8de0100008d","5e5d63ddad47bcde01000122","5e5f86ed8d89c5de0100002e","5e5fd8e65241b5de0100001c","5e60ecfe839e59df01000140","5e61652b417d19de01000061","5e64d2ac0b8008df01000036","5e6741214d24a6df01000086","5e676b211dcaf4de010001ef","5e67802710be53de010000fe","5e68480a9cef79de01000273","5e68d91fae547ede010002af","5e69ce636423dfde010001a0","5e6b12e986bf9cde01000035","5e6b62aac024f9de01000010","5e6b9bf038517edf0100001b","79eiZqbXtAgB2qPwQ","7KTqYg8mwkZFhEzQ3","8M6CKnvXwvJZjw5rQ","8ZH5wCb244dTyjZTo","8gLLyGmGk6zrBNnSW","93wznsAiG6N6RWh3W","BdW2bNumN7KSubzZi","Brx9MCCWjaRcQLgmv","BunZ7u5vo6YP89dqC","CdmkqgCC7YQ3nCxbq","DNPrMfAuXetAfDs8R","E5dirXnhp3dj3aHkh","Fj7MuNTuEZrfjfxxi","HJ3Zeg39qQTmYHYt6","JnXN6mSgNQkfpmqTs","KLFz9Quyco9WRMzEo","MQPkCA7hCG5nHRDGK","MvxLkRFmWAmFzJ62x","NLLPFwcypsnqCdjtt","NgvWrQNZ8WSMvaySr","Qu6vBYRGk4HxjEQHP","RLApear4PKw8oDouR","S5uha8vZYCJgdy3wz","SrePPBjyQrYFJYWuq","TGJLqTRjTSCvjnKnM","TLPpMRduCgvt23KNA","ThXjmMxsKShGXGo9R","WCpGFZGKoopYdccrA","WkmF3PHxRiTFvpvMu","X3CoQQujbB6uEfeCq","XKcJSHf8DcpdPnfNm","XmtnqTvJBkZkvLBZP","YfXHeLKqBXYYzPAww","Zsrup8X5fqoNSkFPe","bHfLw2QkQGko4KjYg","cGwiLTEeZWEYwb88s","cqKH7BXTaAZGZDGzc","eDEjrBSoXdYAJegvm","ev4vmj6dMZpbEWwmy","fKj3TXX3ietf3qGt8","fM3TRWpPB6oRA8rB9","i4ftws6i5ecsWkmYD","k4yef9HxWgNCdW8b3","mReJFExBwnFax3ALu","mZCESDX4P5jLi3pce","nm4T2AcjanPHL4Szj","oaugrfPtDqADRQgJ4","ofGYJBrWWZQYsEGFR","pKG2zHMNxFQDkZHyb","rhhh4xdaNHz94oEm2","rrvwjEikXmbdXZkGx","tCt2KazanazJ3yQzz","vdvk9eCQyAxmSxLqs","xeyEua6SaCWFan2H4"],"dataSources":["MwHF28s95RpwxtWh3","ya2CyA73rpZseyrZ8","2252seNhipfTmjEBQ"]}