1,4-bis(diethylaminophosphino)-2,3,5,6-tetramethylbenzene | 905619-80-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,4-bis(diethylaminophosphino)-2,3,5,6-tetramethylbenzene
• 英文别名: N-[[4-[bis(diethylamino)phosphanyl]-2,3,5,6-tetramethylphenyl]-(diethylamino)phosphanyl]-N-ethylethanamine
• CAS: 905619-80-9
• 化学式: C₂₆H₅₂N₄P₂
• 分子量: 482.673
• InChiKey: ABZGIWWQUDTCPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  13
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis(diethylaminophosphino)-2,3,5,6-tetramethylbenzene 在 盐酸 、 lithium aluminium tetrahydride 、 甲基锂 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 [4-Bis(trimethylsilyl)phosphanyl-2,3,5,6-tetramethylphenyl]-bis(trimethylsilyl)phosphane
  参考文献：
  名称：

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

  摘要：

  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 PdC rather than CdC bonds space phenylene moieties. Specifically, PPPs [sC(6)R(4)-P=C(OSiMe3)sC(6)R'(4)s C(OSiMe3)=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-C6R4[P(SiMe3)(2)](2), and diacid chloride 1,4-C6R4[COCl](2). Several model compounds for PPP are reported. Namely, mono(phosphaalkene)s RsPdC(OSiMe3)s R' (4: R= Ph, R' = Mes; 7: R = Mes, R' = Ph), C-centered bis(phosphaalkene)s RsPdC(OSiMe3)-C6R'(4)-C(OSiMe3) dPsR (5: R = Ph, R' = Me; 8: R = Mes, R' = H), and P-centered bis(phosphaalkene)s R-C( OSiMe3) dPsC(6)R'4-P=C(OSiMe3) sR (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 PdC plane and unsubstituted arenes are 16 degrees-26 degrees, while those between the PdC plane and methyl-substituted arenes are 59-67. 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).

  DOI：

  10.1021/ja060816l
• 作为产物：
  描述：

  双(二乙基氨基)氯膦 、 3,6-二溴四甲苯 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以85%的产率得到1,4-bis(diethylaminophosphino)-2,3,5,6-tetramethylbenzene
  参考文献：
  名称：

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

  摘要：

  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 PdC rather than CdC bonds space phenylene moieties. Specifically, PPPs [sC(6)R(4)-P=C(OSiMe3)sC(6)R'(4)s C(OSiMe3)=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-C6R4[P(SiMe3)(2)](2), and diacid chloride 1,4-C6R4[COCl](2). Several model compounds for PPP are reported. Namely, mono(phosphaalkene)s RsPdC(OSiMe3)s R' (4: R= Ph, R' = Mes; 7: R = Mes, R' = Ph), C-centered bis(phosphaalkene)s RsPdC(OSiMe3)-C6R'(4)-C(OSiMe3) dPsR (5: R = Ph, R' = Me; 8: R = Mes, R' = H), and P-centered bis(phosphaalkene)s R-C( OSiMe3) dPsC(6)R'4-P=C(OSiMe3) sR (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 PdC plane and unsubstituted arenes are 16 degrees-26 degrees, while those between the PdC plane and methyl-substituted arenes are 59-67. 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).

  DOI：

  10.1021/ja060816l