9-(4-nitrophenyl)-3,3,6,6,-tetramethyl-10-(2-thioctinoylaminophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-(4-nitrophenyl)-3,3,6,6,-tetramethyl-10-(2-thioctinoylaminophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione
• 英文别名: 5-(dithiolan-3-yl)-N-[2-[3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxo-4,5,7,9-tetrahydro-2H-acridin-10-yl]phenyl]pentanamide
• 化学式: C₃₇H₄₃N₃O₅S₂
• 分子量: 673.898
• InChiKey: OGPOGSGVBDUSCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  47
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(4-nitrophenyl)-3,3,6,6,-tetramethyl-10-(2-thioctinoylaminophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione 在 calcium chloride 、 锌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 ADDTU
  参考文献：
  名称：

  Selective fluoride ion recognition by a thiourea based receptor linked acridinedione functionalized gold nanoparticles

  摘要：

  The design and synthesis of acridinedione functionalized gold nanoparticles based PET anion sensor 6 is described. The sensor 6 employs simple aromatic thiourea as anion receptors and the fluorophore is the acridinedione moiety, which were characterized by transmission electron microscopy (TEM), Fourier transform infrared (FT-IR), UV-vis, steady-state and time-resolved fluorescence techniques. Upon selective recognition of F in acetonitrile, the fluorescence emission of 6 was quenched with significant changes in the absorption spectrum. These changes are ascribed due to the hydrogen bonding and deprotonation of the thiourea receptor of ADDTU-GNPs. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.10.025
• 作为产物：
  描述：

  2-[(4,4-dimethyl-2,6-dioxocyclohexyl)-(4-nitrophenyl)methyl]-5,5-dimethylcyclohexane-1,3-dione 在 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 9-(4-nitrophenyl)-3,3,6,6,-tetramethyl-10-(2-thioctinoylaminophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione
  参考文献：
  名称：

  Metal ion-induced dual fluorescent change for aza-crown ether acridinedione-functionalized gold nanorods and quantum dots

  摘要：

  氮杂冠醚吖啶二酮功能化量子点（ACEADD-QD）和氮杂冠醚吖啶二酮功能化金纳米棒（ACEADD-GNR）已被开发成一对，用于检测金属离子的荧光化学传感器。 ACEADD-QD 在吖啶二酮染料部分的可见波长~430 nm 处和 CdTeSe QD 的近红外 (NIR) 波长~775 nm 处具有双重发射。在Ca2+或Mg2+离子存在下，ACEADD-QD和ACEADD-GNR对可以形成由金属离子介导的夹心复合物。 ACEADD-QD 和 ACEADD-GNR 复合物对显示吖啶二酮染料的可见荧光增强和 NIR QD 的并发荧光猝灭。氮杂冠醚络合物导致抑制从氮杂冠醚到吖啶二酮染料部分的光诱导电子转移。同时，纳米金属表面能从QD转移到GNR可以有效猝灭QD荧光。该ACEADD-QD和ACEADD-GNR对可以有效地将冠醚与金属离子的选择性结合事件转化为同时调节染料荧光的增强和QD发射的猝灭，这可以为比例传感器开辟新的策略对环境条件具有选择性和鲁棒性。

  DOI：

  10.1039/c2nj40444c

文献信息

• Colorimetric and fluorometric chemosensors for selective signaling toward Ca2+ and Mg2+ by aza-crown ether acridinedione-functionalized gold nanoparticles
  作者：Ranganathan Velu、Vayalakkavoor T. Ramakrishnan、Perumal Ramamurthy

  DOI：10.1016/j.tetlet.2010.06.041

  日期：2010.8

  The aza-crown ether acridinedione-functionalized gold nanoparticles (ACEADD-GNPs) 6 have been synthesized and investigated as a fluorescent chemosensor for metal ions A blue shift along with an intensity enhancement of emission and color change are observed in the presence of both Ca2+ and Mg2+ ions The enhanced fluorescence intensity is attributed to the photoinduced electron transfer (PET) suppression through space and color change of the suspension from red to blue due to shifted surface plasmon resonance (SPR) with aggregation of nanoparticles by the sandwich complexation (c) 2010 Elsevier Ltd All rights reserved
• Metal ion-induced dual fluorescent change for aza-crown ether acridinedione-functionalized gold nanorods and quantum dots
  作者：Ranganathan Velu、Nayoun Won、Jungheon Kwag、Sungwook Jung、Jaehyun Hur、Sungjee Kim、Nokyoung Park

  DOI：10.1039/c2nj40444c

  日期：——

  Aza-crown ether acridinedione-functionalized quantum dots (ACEADD-QDs) and aza-crown ether acridinedione-functionalized gold nanorods (ACEADD-GNRs) have been developed as a pair for a fluorescent chemosensor detecting metal ions. The ACEADD-QDs have dual emissions at a visible wavelength of ∼430 nm from the acridinedione dye moiety and at a near-infrared (NIR) wavelength of ∼775 nm from the CdTeSe QDs. In the presence of Ca2+ or Mg2+ ions, the ACEADD-QD and ACEADD-GNR pair can form a sandwich complex mediated by the metal ion. The ACEADD-QD and ACEADD-GNR complex pair shows visible fluorescence enhancement from the acridinedione dye and concurrent fluorescence quenching from the NIR QD. The aza-crown ether complex results in the suppression of photoinduced electron transfer from the aza-crown ether to the acridinedione dye moiety. At the same time, the QD fluorescence can be effectively quenched by the nanometal surface energy transfer from the QD to the GNR. This ACEADD-QD and ACEADD-GNR pair can effectively transduce the selective binding event of crown ethers with metal ions into the simultaneous modulation of the enhancement in dye fluorescence and the quenching of QD emission, which can open a new strategy for ratiometric sensors that are selective and robust against the environment conditions.

  氮杂冠醚吖啶二酮功能化量子点（ACEADD-QD）和氮杂冠醚吖啶二酮功能化金纳米棒（ACEADD-GNR）已被开发成一对，用于检测金属离子的荧光化学传感器。 ACEADD-QD 在吖啶二酮染料部分的可见波长~430 nm 处和 CdTeSe QD 的近红外 (NIR) 波长~775 nm 处具有双重发射。在Ca2+或Mg2+离子存在下，ACEADD-QD和ACEADD-GNR对可以形成由金属离子介导的夹心复合物。 ACEADD-QD 和 ACEADD-GNR 复合物对显示吖啶二酮染料的可见荧光增强和 NIR QD 的并发荧光猝灭。氮杂冠醚络合物导致抑制从氮杂冠醚到吖啶二酮染料部分的光诱导电子转移。同时，纳米金属表面能从QD转移到GNR可以有效猝灭QD荧光。该ACEADD-QD和ACEADD-GNR对可以有效地将冠醚与金属离子的选择性结合事件转化为同时调节染料荧光的增强和QD发射的猝灭，这可以为比例传感器开辟新的策略对环境条件具有选择性和鲁棒性。
• Selective fluoride ion recognition by a thiourea based receptor linked acridinedione functionalized gold nanoparticles
  作者：R. Velu、V.T. Ramakrishnan、P. Ramamurthy

  DOI：10.1016/j.jphotochem.2010.10.025

  日期：2011.1

  The design and synthesis of acridinedione functionalized gold nanoparticles based PET anion sensor 6 is described. The sensor 6 employs simple aromatic thiourea as anion receptors and the fluorophore is the acridinedione moiety, which were characterized by transmission electron microscopy (TEM), Fourier transform infrared (FT-IR), UV-vis, steady-state and time-resolved fluorescence techniques. Upon selective recognition of F in acetonitrile, the fluorescence emission of 6 was quenched with significant changes in the absorption spectrum. These changes are ascribed due to the hydrogen bonding and deprotonation of the thiourea receptor of ADDTU-GNPs. (C) 2010 Elsevier B.V. All rights reserved.