1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)naphthalene | 1254204-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)naphthalene
• 英文别名: p-NBimM；1-[[4-[(5,6-Dimethylbenzimidazol-1-yl)methyl]naphthalen-1-yl]methyl]-5,6-dimethylbenzimidazole；1-[[4-[(5,6-dimethylbenzimidazol-1-yl)methyl]naphthalen-1-yl]methyl]-5,6-dimethylbenzimidazole
• CAS: 1254204-77-7
• 化学式: C₃₀H₂₈N₄
• 分子量: 444.579
• InChiKey: LOWFCZSKUKHBAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  十羰基二铼 、 1,4-二羟基蒽醌 、 1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)naphthalene 以 甲苯 为溶剂， 以66%的产率得到[Re(CO)3]2(μ-1,4-dihydroxy-9,10-anthraquinone(2-))(μ-1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)napthalene)
  参考文献：
  名称：

  Quinonoid-Bridged Chair-Shaped Dirhenium(I) Metallacycles: Synthesis, Characterization, and Spectroelectrochemical Studies

  摘要：

  Self-assembled, chair-shaped dirhenium(I) macrocyclic compounds featuring the two different bis-chelating quinone dianions (1, L = dhnq(2-); 2, L = dhaq(2-); H(2)dhnq = 6,11-dihydroxy-5,12-naphthacenedione; H(2)dhaq = 1,4-dihydroxy-9,10-anthraquinone) that interface with two fac-Re(CO)(3) cores and a ditopic semirigid N-donor 1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)naphthalene (L' = p-NBimM) ligand coordinated to the remaining orthogonal site were prepared in high yields. Their structures were confirmed by single-crystal X-ray diffraction analysis. Electrochemical assessments, using cyclic voltammetry (CV) and UV-vis-NIR spectroelectrochemistry (SEC), revealed the existence of two well-separated, single-electron quinone ligand-centered, reversibly accessible 0, -1, and -2 redox states. Among the two singly reduced radical complexes, the symmetrically bridged quinone complex 1(center dot-), showed a strong absorption in the NIR regions, which was not observed for the neutral and doubly reduced states, analogous to that of the free dhnq(3 center dot-) quinone. In contrast, when 2 was reduced to 2(center dot-), a broad signal at 866 nm was observed, very similar to the reduced dhaq(3 center dot-) quinone. This difference in spectral behavior in the singly reduced states is likely due to the annealed benzene ring in 1 and dhnq(2-) because of its symmetrical pi-electron system, which is perturbed to a lesser degree compared to asymmetric 2 and dhaq(2-). Reduction to 1(center dot-) produces a small but not negligible g factor anisotropy (Delta g = 0.024) in the electron spin resonance (ESR) signal, indicative of a very small metal-centered spin (5%), but 2(center dot-) shows a g value in the expected range for organic radicals (no detectable Delta g). Thus, the combined investigations reveal that the singly reduced metallacycles are best described as being highly stable, noncommunicating, localized, quinonoid-centered radical complexes, [(CO)(3)Re-I(mu-L3 center dot-)(mu-L')Re-I(CO)(3)](center dot-).

  DOI：

  10.1021/ic9018794
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 、 1,4-双(溴甲基)萘 在 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以24%的产率得到1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)naphthalene
  参考文献：
  名称：

  Quinonoid-Bridged Chair-Shaped Dirhenium(I) Metallacycles: Synthesis, Characterization, and Spectroelectrochemical Studies

  摘要：

  Self-assembled, chair-shaped dirhenium(I) macrocyclic compounds featuring the two different bis-chelating quinone dianions (1, L = dhnq(2-); 2, L = dhaq(2-); H(2)dhnq = 6,11-dihydroxy-5,12-naphthacenedione; H(2)dhaq = 1,4-dihydroxy-9,10-anthraquinone) that interface with two fac-Re(CO)(3) cores and a ditopic semirigid N-donor 1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)naphthalene (L' = p-NBimM) ligand coordinated to the remaining orthogonal site were prepared in high yields. Their structures were confirmed by single-crystal X-ray diffraction analysis. Electrochemical assessments, using cyclic voltammetry (CV) and UV-vis-NIR spectroelectrochemistry (SEC), revealed the existence of two well-separated, single-electron quinone ligand-centered, reversibly accessible 0, -1, and -2 redox states. Among the two singly reduced radical complexes, the symmetrically bridged quinone complex 1(center dot-), showed a strong absorption in the NIR regions, which was not observed for the neutral and doubly reduced states, analogous to that of the free dhnq(3 center dot-) quinone. In contrast, when 2 was reduced to 2(center dot-), a broad signal at 866 nm was observed, very similar to the reduced dhaq(3 center dot-) quinone. This difference in spectral behavior in the singly reduced states is likely due to the annealed benzene ring in 1 and dhnq(2-) because of its symmetrical pi-electron system, which is perturbed to a lesser degree compared to asymmetric 2 and dhaq(2-). Reduction to 1(center dot-) produces a small but not negligible g factor anisotropy (Delta g = 0.024) in the electron spin resonance (ESR) signal, indicative of a very small metal-centered spin (5%), but 2(center dot-) shows a g value in the expected range for organic radicals (no detectable Delta g). Thus, the combined investigations reveal that the singly reduced metallacycles are best described as being highly stable, noncommunicating, localized, quinonoid-centered radical complexes, [(CO)(3)Re-I(mu-L3 center dot-)(mu-L')Re-I(CO)(3)](center dot-).

  DOI：

  10.1021/ic9018794

文献信息

• Quinonoid-Bridged Chair-Shaped Dirhenium(I) Metallacycles: Synthesis, Characterization, and Spectroelectrochemical Studies
  作者：Dibyendu Bhattacharya、Malaichamy Sathiyendiran、Jing-Yun Wu、Che-Hao Chang、Sung-Chou Huang、Yu-Ling Zeng、Ching-Yao Lin、P. Thanasekaran、Bo-Chao Lin、Chao-Ping Hsu、Gene-Hsiang Lee、Shie-Ming Peng、Kuang-Lieh Lu

  DOI：10.1021/ic9018794

  日期：2010.11.15

  Self-assembled, chair-shaped dirhenium(I) macrocyclic compounds featuring the two different bis-chelating quinone dianions (1, L = dhnq(2-); 2, L = dhaq(2-); H(2)dhnq = 6,11-dihydroxy-5,12-naphthacenedione; H(2)dhaq = 1,4-dihydroxy-9,10-anthraquinone) that interface with two fac-Re(CO)(3) cores and a ditopic semirigid N-donor 1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)naphthalene (L' = p-NBimM) ligand coordinated to the remaining orthogonal site were prepared in high yields. Their structures were confirmed by single-crystal X-ray diffraction analysis. Electrochemical assessments, using cyclic voltammetry (CV) and UV-vis-NIR spectroelectrochemistry (SEC), revealed the existence of two well-separated, single-electron quinone ligand-centered, reversibly accessible 0, -1, and -2 redox states. Among the two singly reduced radical complexes, the symmetrically bridged quinone complex 1(center dot-), showed a strong absorption in the NIR regions, which was not observed for the neutral and doubly reduced states, analogous to that of the free dhnq(3 center dot-) quinone. In contrast, when 2 was reduced to 2(center dot-), a broad signal at 866 nm was observed, very similar to the reduced dhaq(3 center dot-) quinone. This difference in spectral behavior in the singly reduced states is likely due to the annealed benzene ring in 1 and dhnq(2-) because of its symmetrical pi-electron system, which is perturbed to a lesser degree compared to asymmetric 2 and dhaq(2-). Reduction to 1(center dot-) produces a small but not negligible g factor anisotropy (Delta g = 0.024) in the electron spin resonance (ESR) signal, indicative of a very small metal-centered spin (5%), but 2(center dot-) shows a g value in the expected range for organic radicals (no detectable Delta g). Thus, the combined investigations reveal that the singly reduced metallacycles are best described as being highly stable, noncommunicating, localized, quinonoid-centered radical complexes, [(CO)(3)Re-I(mu-L3 center dot-)(mu-L')Re-I(CO)(3)](center dot-).