N-(2,5-di-tert-butylphenyl)-N'-(4-carboxymethyl)naphthalene-1,8:4,5-tetracarboxydiimide | 706787-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(2,5-di-tert-butylphenyl)-N'-(4-carboxymethyl)naphthalene-1,8:4,5-tetracarboxydiimide
• 英文别名: HO2CCH2(C14H4N2)O4(C6H3)(t-Bu)2；2-[13-(2,5-Ditert-butylphenyl)-5,7,12,14-tetraoxo-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaen-6-yl]acetic acid；2-[13-(2,5-ditert-butylphenyl)-5,7,12,14-tetraoxo-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaen-6-yl]acetic acid
• CAS: 706787-26-0
• 化学式: C₃₀H₂₈N₂O₆
• 分子量: 512.562
• InChiKey: ZSGAYNCJKCVTEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  、 N-(2,5-di-tert-butylphenyl)-N'-(4-carboxymethyl)naphthalene-1,8:4,5-tetracarboxydiimide 以 四氢呋喃 为溶剂， 生成 (Zn(II) 2-amidinium-5,10,15,20-tetramesitylporphyrin):(N-(2,5-di-tert-butylphenyl)-N'-(carboxymetyl)naphthalene-1,8:4,5-tetracarboxydimide)
  参考文献：
  名称：

  氢键结合的供体-受体组装体中质子波动驱动电子转移。

  摘要：

  报道了非共价分子二元体的质子耦合电子转移（PCET）的温度-同位素依赖性。该系统由激发态的卟啉锌（II）组成，该卟啉通过electron-羧酸盐界面将电子转移至萘二酰亚胺受体。对于不同的温度范围，观察到两种不同的同位素效应。当T接近120 K（kH / kD = 0.9，120 K）时，观察到反向同位素效应（即，kH / kD <1），而随着温度的升高，恢复了正常的同位素效应（即，kH / kD> 1）。增加（kH / kD = 1.2，300 K）。这些极限之间的过渡是平滑的，T的交越温度约为160K。这些观察结果符合电荷转移动力学，该动力学易于受镀液诱导的质子坐标波动的影响。

  DOI：

  10.1021/jp056703q
• 作为产物：
  描述：

  聚甘氨酸 、 N-(2,5-di-tert-butylphenyl)-naphthalene-1,8-dicarboxyanhydride-4,5-dicarboximide 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2,5-di-tert-butylphenyl)-N'-(4-carboxymethyl)naphthalene-1,8:4,5-tetracarboxydiimide
  参考文献：
  名称：

  Young, Elizabeth R.; Rosenthal, Joel; Hodgkiss, Justin M., Journal of the American Chemical Society, 2009, vol. 131, p. 7678 - 7684

  摘要：

  DOI：

文献信息

• Observation of Proton-Coupled Electron Transfer by Transient Absorption Spectroscopy in a Hydrogen-Bonded, Porphyrin Donor−Acceptor Assembly
  作者：Niels H. Damrauer、Justin M. Hodgkiss、Joel Rosenthal、Daniel G. Nocera

  DOI：10.1021/jp049296b

  日期：2004.5.1

  Proton-coupled electron transfer (PCET) kinetics of a Zn(II) porphyrin donor noncovalently bound to a naphthalene-diimide acceptor through an amidinium-carboxylate interface have been investigated by time-resolved spectroscopy. The S, singlet excited-state of a Zn(II) 2-amidinium-5,10,15,20-tetramesitylporphyrin chloride (ZnP-beta-AmH+) donor is sufficiently energetic (2.04 eV) to reduce a carboxylate-diimide acceptor (DeltaGdegrees = -460 mV, THF). Static quenching of the porphyrin fluorescence is observed and time-resolved measurements reveal more than a 3-fold reduction in the S, lifetime of the porphyrin upon amidinium-carboxylate formation (THF, 298 K). Picosecond transient absorption spectra of the free ZnP-beta-AmH+ in THF reveal the existence of an excited-state isosbestic point between the S-1 and T-1 states at probe = 650 nm, providing an effective 'zero-kinetics' background on which to observe the formation of PCET photoproducts. Distinct rise and decay kinetics are attributed to the build-up and subsequent loss of intermediates resulting from a forward and reverse PCET reaction, respectively (k(PCET)(fwd) = 9 x 10(8) s(-1) and k(PCET)(rev) = 14 x 101 s-1). The forward rate constant is nearly 2 orders of magnitude slower than that measured for covalently linked Zn(II) porphyrin-acceptor dyads of comparable driving force and D-A distance, establishing the importance of a proximal proton network in controlling charge transport.
• Electron Transfer Driven by Proton Fluctuations in a Hydrogen-Bonded Donor−Acceptor Assembly
  作者：Justin M. Hodgkiss、Niels H. Damrauer、Steve Pressé、Joel Rosenthal、Daniel G. Nocera

  DOI：10.1021/jp056703q

  日期：2006.9.28

  The temperature-isotope dependence of proton-coupled electron transfer (PCET) for a noncovalent molecular dyad is reported. The system consists of an excited-state Zn(II) porphyrin that transfers an electron to a naphthalene diimide acceptor through an amidinium-carboxylate interface. Two different isotope effects are observed for variant temperature regimes. A reverse isotope effect (i.e., kH/kD <

  报道了非共价分子二元体的质子耦合电子转移（PCET）的温度-同位素依赖性。该系统由激发态的卟啉锌（II）组成，该卟啉通过electron-羧酸盐界面将电子转移至萘二酰亚胺受体。对于不同的温度范围，观察到两种不同的同位素效应。当T接近120 K（kH / kD = 0.9，120 K）时，观察到反向同位素效应（即，kH / kD <1），而随着温度的升高，恢复了正常的同位素效应（即，kH / kD> 1）。增加（kH / kD = 1.2，300 K）。这些极限之间的过渡是平滑的，T的交越温度约为160K。这些观察结果符合电荷转移动力学，该动力学易于受镀液诱导的质子坐标波动的影响。
• Young, Elizabeth R.; Rosenthal, Joel; Hodgkiss, Justin M., Journal of the American Chemical Society, 2009, vol. 131, p. 7678 - 7684
  作者：Young, Elizabeth R.、Rosenthal, Joel、Hodgkiss, Justin M.、Nocera, Daniel G.

  DOI：——

  日期：——