Crystal structure of p-bis(tert-butyl-trimethylsiloxyl-methyliden-phosphino)-benzene,(C4H9C((CH3)3SiO)P)2C6H4

Knoch, Falk; Appel, Rolf; Wenzel, Herbert R.

doi:10.1524/zkri.1995.210.3.224

Cited by 4 publications

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“…A summary of data collection and refinement parameters is listed in Table , and the bond lengths and angles for these and other phosphaalkenes pertinent to this discussion are summarized in Table . A survey of the Cambridge Crystallographic Database (CCD) for possible molecular models for the PPP s reported herein revealed 22 Becker-type phosphaalkenes. 40b,,− Of these, just seven feature carbon substituents on both the phosphorus and carbon atoms of the PC bond ( 12 , 13 , 14 , 15 , 16 ,40b 17 , and 18 57 ). To our knowledge, two other 1,4-arylene-bridged bis(phosphaalkene)s have previously been crystallographically characterized ( 18 57 and 19 ).…”

Section: Resultsmentioning

confidence: 94%

Phosphorus Copies of PPV: π-Conjugated Polymers and Molecules Composed of Alternating Phenylene and Phosphaalkene Moieties

et al. 2006

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A new class of pi-conjugated macromolecule, poly(p-phenylenephosphaalkene) (PPP), is reported. PPPs are phosphorus analogues of the important electronic material poly(p-phenylenevinylene) (PPV) where P=C rather than C=C bonds space phenylene moieties. Specifically, PPPs [-C(6)R(4)-P=C(OSiMe(3))-C(6)R'(4)-C(OSiMe(3))=P-](n)() (1: R = H, R' = Me; 11: R = Me, R' = H) were synthesized by utilizing the Becker reaction of a bifunctional silylphosphine, 1,4-C(6)R(4)[P(SiMe(3))(2)](2), and diacid chloride 1,4-C(6)R'(4)[COCl](2). Several model compounds for PPP are reported. Namely, mono(phosphaalkene)s R-P=C(OSiMe(3))-R' (4: R = Ph, R' = Mes; 7: R = Mes, R' = Ph), C-centered bis(phosphaalkene)s R-P=C(OSiMe(3))-C(6)R'(4)-C(OSiMe(3))=P-R (5: R = Ph, R' = Me; 8: R = Mes, R' = H), and P-centered bis(phosphaalkene)s R-C(OSiMe(3))=P-C(6)R'(4)-P=C(OSiMe(3))-R (6: R = Mes, R' = H; 10: R = Ph, R' = Me). Remarkably, selective Z-isomer formation (i.e., trans arylene moieties) is observed for PPPs when bulky P-substituents are employed while E/Z-mixtures are otherwise obtained. X-ray crystal structures of Z-7, Z,Z-8, and Z,Z-10 suggest moderate pi-conjugation. The twist angles between the P=C plane and unsubstituted arenes are 16 degrees -26 degrees , while those between the P=C plane and methyl-substituted arenes are 59 degrees -67 degrees . The colored PPPs and their model compounds were studied by UV/vis spectroscopy, and the results are consistent with extended pi-conjugation. Specifically, weakly emissive polymer E/Z-1 (lambda(max) = 338 nm) shows a red shift in its absorbance from model E/Z-4 (lambda(max) = 310 nm), while a much larger red shift is observed for Z-11 (lambda(max) = 394 nm) over Z-7 (lambda(max) = 324 nm).

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Section: Resultsmentioning

confidence: 94%

Phosphorus Copies of PPV: π-Conjugated Polymers and Molecules Composed of Alternating Phenylene and Phosphaalkene Moieties

et al. 2006

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“…Examples of molecules possessing two or more phosphaalkene moieties bridged by arylene spacers are uncommon;12 furthermore, there are only two previous reports of bis(phosphaalkene)s prepared through [1,3]‐silatropic rearrangement 11b, 12b. Thus, we set out to prepare 2 from a concentrated solution of PhP(SiMe 3 ) 2 (2 equiv) and 4 in THF and hexanes.…”

Section: Methodsmentioning

confidence: 99%

Poly(p-phenylenephosphaalkene): A π-Conjugated Macromolecule Containing PC Bonds in the Main Chain

Wright

Gates

2002

Angew. Chem. Int. Ed.

170

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An unprecedented yellow polymer with low‐coordinate phosphorus atoms in the backbone has been prepared. The material is soluble in polar organic solvents, and moderate molecular weights (Mn=2900–10 500 g mol−1) were estimated from 31P NMR spectroscopic end‐group analysis. The possible π‐conjugation was investigated by UV/Vis spectroscopy, which revealed a red shift in λmax for the polymer when compared with colorless molecular‐model systems (see picture; left: model system, right: new polymer, in THF).

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Poly(p-phenylenephosphaalkene): A π-Conjugated Macromolecule Containing PC Bonds in the Main Chain

Wright

Gates

2002

Angew. Chem.

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Crystal structure of p-bis(tert-butyl-trimethylsiloxyl-methyliden-phosphino)-benzene,(C₄H₉C((CH₃)₃SiO)P)₂C₆H₄

Cited by 4 publications

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Phosphorus Copies of PPV: π-Conjugated Polymers and Molecules Composed of Alternating Phenylene and Phosphaalkene Moieties

Phosphorus Copies of PPV: π-Conjugated Polymers and Molecules Composed of Alternating Phenylene and Phosphaalkene Moieties

Poly(p-phenylenephosphaalkene): A π-Conjugated Macromolecule Containing PC Bonds in the Main Chain

Poly(p-phenylenephosphaalkene): A π-Conjugated Macromolecule Containing PC Bonds in the Main Chain

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