{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:30:14Z","timestamp":1788309014725,"version":"build-2803163510"},"reference-count":61,"publisher":"Wiley","issue":"33","license":[{"start":{"date-parts":[[2014,7,17]],"date-time":"2014-07-17T00:00:00Z","timestamp":1405555200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2014,8,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Phosphorus analogues of pyrromellitic diimides (PyDIs), which represent a family of privileged electron\u2010accepting organic compounds, have been successfully synthesized as novel electron\u2010accepting \u03c0\u2010conjugated molecules. Investigation into their physicochemical properties uncovered their prominent electron\u2010accepting abilities over the corresponding PyDI. Furthermore, theoretical studies revealed the significant contribution of \u03c3*\u2013\u03c0* hyperconjugation in stabilizing the LUMO+1.<\/jats:p>","DOI":"10.1002\/chem.201403735","type":"journal-article","created":{"date-parts":[[2014,7,17]],"date-time":"2014-07-17T16:30:08Z","timestamp":1405614608000},"page":"10266-10270","source":"Crossref","is-referenced-by-count":45,"title":["2,6\u2010Diphospha\u2010<i>s<\/i>\u2010indacene\u20101,3,5,7(2\u2009<i>H<\/i>,6\u2009<i>H<\/i>)\u2010tetraone: A Phosphorus Analogue of Aromatic Diimides with the Minimal Core Exhibiting High Electron\u2010Accepting Ability"],"prefix":"10.1002","volume":"20","author":[{"given":"Youhei","family":"Takeda","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takuya","family":"Nishida","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Satoshi","family":"Minakata","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,7,17]]},"reference":[{"key":"e_1_2_3_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr040179m"},{"key":"e_1_2_3_2_2","unstructured":"For reviews on phospholes see:"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0032-1317804"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2dt00024e"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200900179"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b819255n"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/b810976a"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200700236"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200200557"},{"key":"e_1_2_3_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200200557"},{"key":"e_1_2_3_10_2","unstructured":"For reviews on electron\u2010accepting organic materials see:"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cp51379c"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cp41664f"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200903628"},{"key":"e_1_2_3_14_2","unstructured":"For reviews on aromatic diimides see:"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201001402"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo2001963"},{"key":"e_1_2_3_17_2","unstructured":"\u00a0"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja805746h"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/mz200007p"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/mz400164s"},{"key":"e_1_2_3_21_2","unstructured":"\u00a0"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja310680x"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/om400991a"},{"key":"e_1_2_3_24_2","unstructured":"\u00a0"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39870001753"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc32247a"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536804018616"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)81139-4"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19761090137"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19744080307"},{"key":"e_1_2_3_31_2","unstructured":"For details see the Supporting Information."},{"key":"e_1_2_3_32_2","unstructured":"\u00a0"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19784430107"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/hc.20606"},{"key":"e_1_2_3_35_2","unstructured":"At the preliminary stage of our research we attempted the condensation using bis(trimethylsilyl)phenylphosphine PhP(SiMe3)2 instead of MesP(SiMe3)2. However PhP(SiMe3)2was highly sensitive to air and moisture as reported by Baumgartner (ref.\u20057a). Taking into account the stability of both disilylphosphine reagents and forming products we chose MesP(SiMe3)2as the phosphorus source in this study."},{"key":"e_1_2_3_36_2","unstructured":"The DFT calculation performed at the B3LYP\/6\u201331G(d) level suggested that theantiisomer of2is more thermodynamically stable than thesynisomer in the gas phase by 0.43\u2005kcal\u2009mol\u22121."},{"key":"e_1_2_3_37_2","unstructured":"Attempts to complex1with [Au(tht)Cl] resulted in precipitation of a yellow solid but it was not soluble in any organic solvents."},{"key":"e_1_2_3_38_2","unstructured":"\u00a0"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203047"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201104114"},{"key":"e_1_2_3_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201104114"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201000196"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.crci.2010.04.021"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol7030608"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800841v"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0352658"},{"key":"e_1_2_3_46_2","unstructured":"For a summary of the crystal data ofanti\u20101 see the Supporting Information. CCDC\u2010992024 contains the supplementary crystallographic data for this paper. These data are available free of charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_3_47_2","unstructured":"Line\u2010shape simulations were performed using the WINDNMR\u2010Pro program: H.\u2005J. Reich J. Chem. Educ. Software\u00ad1996 3D 2; http:\/\/www.chem.wisc.edu\/areas\/reich\/plt\/windnmr.htm."},{"key":"e_1_2_3_48_2","unstructured":"For reviews on pyramidal inversion see:"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19700821202"},{"key":"e_1_2_3_49_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197004001"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.2164-0947.1973.tb01961.x"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00713a028"},{"key":"e_1_2_3_52_2","unstructured":"\u00a0"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00708a077"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00752a035"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00752a035"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)86243-2"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/1616-3028(200102)11:1<15::AID-ADFM15>3.0.CO;2-A"},{"key":"e_1_2_3_58_2","unstructured":"As for1and2 only the results ofantiisomers were depicted because of the negligible differences in energies and orbitals of two stereoisomers. 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