9H-indeno-9-one-[1,2-b]:1,4-diaza-11H-fluoreno[2,3-g]quinoxalin-11-one | 1156494-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 9H-indeno-9-one-[1,2-b]:1,4-diaza-11H-fluoreno[2,3-g]quinoxalin-11-one
• 英文别名: 4,14,18,28-Tetrazaheptacyclo[15.11.0.03,15.05,13.06,11.019,27.021,26]octacosa-1(17),2,4,6,8,10,13,15,18,21,23,25,27-tridecaene-12,20-dione
• CAS: 1156494-19-7
• 化学式: C₂₄H₁₀N₄O₂
• 分子量: 386.369
• InChiKey: VJZPYMSUOWSFLU-UHFFFAOYSA-N

物化性质

• 沸点：
  711.6±55.0 °C(predicted)
• 密度：
  1.600±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9H-indeno-9-one-[1,2-b]:1,4-diaza-11H-fluoreno[2,3-g]quinoxalin-11-one 、 dimethyl (1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarboxylate 以 邻二氯苯 为溶剂， 反应 2.0h， 以16%的产率得到spiro[dimethyl-3,10-dimethoxy-1α,12α,13β,14α,17α,18β-16,19-dioxahexacyclo[10,6,1.1^14,170^2,110^4,90^13,18]-dodeca-2,4,6,8,10-pentaene-14,17-dicarboxylate-15,11'-9'H-indeno-9'-one-[1',2'-b]:1',4'-diaza-11'H-fluoreno[2',3'-g]quinoxalin]
  参考文献：
  名称：

  Ninhydrin as a building block in scaffold-linked chromophoric dyad construction

  摘要：

  The reaction of ninhydrin with ester-activated cyclobutene epoxide (CE-1) containing the fused 1,4-dimethoxynaphthalene (DMN) chromophore, gave adducts formed by 1,3-dipolar cycloaddition at the central (C-2)-CO (major) and the outer (C-1,C-3)-CO (minor) positions. Conversion of the minor adduct to quinoxalines (QIN) by reaction with o-phenylenediamines at the alpha-dione moiety, albeit in poor yield, led to spiro-DMN-1,4 sigma-QIN dyad in which the plane of the chromophore was orthogonally orientated yet angled to the plane of the DMN chromophore. Reaction of ninhydrin with o-phenylenediamines yielded the corresponding 11-oxoindeno[1,2-b]quinoxalines which were coupled with CE-BLOCKs to form spiro adducts by reaction at the carbonyl site; the product from CE-1 was identical with that formed above. Another class of spiro-fused dyads was produced by reaction of ninhydrin with a primary amine followed by cycloaddition of CE-BLOCKs at the carbonyl site, where the amine was available to deliver one chromophore and the CE-BLOCK another.

  DOI：

  10.3998/ark.5550190.p008.520
• 作为产物：
  描述：

  水合茚三酮 、 1,2,4,5-benzenetetraamine tetrahydrochloride 反应 0.5h， 以13%的产率得到9H-indeno-9-one-[1,2-b]:1,4-diaza-11H-fluoreno[2,3-g]quinoxalin-11-one
  参考文献：
  名称：

  Ninhydrin as a building block in scaffold-linked chromophoric dyad construction

  摘要：

  The reaction of ninhydrin with ester-activated cyclobutene epoxide (CE-1) containing the fused 1,4-dimethoxynaphthalene (DMN) chromophore, gave adducts formed by 1,3-dipolar cycloaddition at the central (C-2)-CO (major) and the outer (C-1,C-3)-CO (minor) positions. Conversion of the minor adduct to quinoxalines (QIN) by reaction with o-phenylenediamines at the alpha-dione moiety, albeit in poor yield, led to spiro-DMN-1,4 sigma-QIN dyad in which the plane of the chromophore was orthogonally orientated yet angled to the plane of the DMN chromophore. Reaction of ninhydrin with o-phenylenediamines yielded the corresponding 11-oxoindeno[1,2-b]quinoxalines which were coupled with CE-BLOCKs to form spiro adducts by reaction at the carbonyl site; the product from CE-1 was identical with that formed above. Another class of spiro-fused dyads was produced by reaction of ninhydrin with a primary amine followed by cycloaddition of CE-BLOCKs at the carbonyl site, where the amine was available to deliver one chromophore and the CE-BLOCK another.

  DOI：

  10.3998/ark.5550190.p008.520

文献信息

• AZAINDENOFLUORENEDIONE DERIVATIVE, ORGANIC ELECTROLUMINESCENT DEVICE MATERIAL, AND ORGANIC ELECTROLUMINESCENT DEVICE
  申请人：Idemitsu Kosan Co., Ltd.

  公开号：EP2213662B1

  公开（公告）日：2012-04-18
• AZAINDENOFLUORENEDIONE DERIVATIVE, MATERIAL FOR ORGANIC ELECTROLUMINESCENCE DEVICE AND ORGANIC ELECTROLUMINESCENCE DEVICE
  申请人：MORISHITA Hironobu

  公开号：US20090315022A1

  公开（公告）日：2009-12-24

  An azaindenofluorenedione derivative shown by the following formula (I), (IIa) or (IIb):
• US8088901B2
  申请人：——

  公开号：US8088901B2

  公开（公告）日：2012-01-03
• [EN] PHOTOACTIVE MATERIAL<br/>[FR] MATÉRIAU PHOTOACTIF
  申请人：[en]CAMBRIDGE DISPLAY TECHNOLOGY LTD.

  公开号：WO2022129594A1

  公开（公告）日：2022-06-23

  A material comprising an electron-accepting unit of formula (I). According to some embodiments, the present disclosure provides a material comprising an electron-accepting unit of formula (I) wherein Ar is a substituted or unsubstituted benzene or 6-membered heteroaromatic ring containing N and C ring atoms; Ar1is a substituted or unsubstituted 5- or 6-membered heteroaromatic ring containing N and C ring atoms; Ar2is a substituted or unsubstituted 5- or 6-membered heteroaromatic ring or is absent; Ar3is a 5-membered ring or a substituted or unsubstituted 6-membered ring; Ar4is a 5-membered ring or a substituted or unsubstituted 6-membered ring or is absent; Ar5is a substituted or unsubstituted monocyclic or polycyclic group containing at least one aromatic or heteroaromatic ring; Ar6is a substituted or unsubstituted monocyclic or polycyclic group containing at least one aromatic or heteroaromatic ring or is absent; and each X is independently a substituent bound to a carbon atom of Ar3and, where present, Ar4with the proviso that at least one X group is an electron-withdrawing group and wherein the material further comprises a conjugated electron-donating unit. The material may be a polymer comprising repeat units of formula (I). The material may be a non-polymeric compound. An organic photodetector may contain a bulk heterojunction layer containing an electron acceptor or an electron donor wherein at least one of the electron acceptor and electron donor contains a unit of formula (I).
• Ninhydrin as a building block in scaffold-linked chromophoric dyad construction
  作者：Davor Margetic、David A. Mann、Ronald N. Warrener

  DOI：10.3998/ark.5550190.p008.520

  日期：——

  The reaction of ninhydrin with ester-activated cyclobutene epoxide (CE-1) containing the fused 1,4-dimethoxynaphthalene (DMN) chromophore, gave adducts formed by 1,3-dipolar cycloaddition at the central (C-2)-CO (major) and the outer (C-1,C-3)-CO (minor) positions. Conversion of the minor adduct to quinoxalines (QIN) by reaction with o-phenylenediamines at the alpha-dione moiety, albeit in poor yield, led to spiro-DMN-1,4 sigma-QIN dyad in which the plane of the chromophore was orthogonally orientated yet angled to the plane of the DMN chromophore. Reaction of ninhydrin with o-phenylenediamines yielded the corresponding 11-oxoindeno[1,2-b]quinoxalines which were coupled with CE-BLOCKs to form spiro adducts by reaction at the carbonyl site; the product from CE-1 was identical with that formed above. Another class of spiro-fused dyads was produced by reaction of ninhydrin with a primary amine followed by cycloaddition of CE-BLOCKs at the carbonyl site, where the amine was available to deliver one chromophore and the CE-BLOCK another.