4-bromo-N-(11-undecylferrocenyl)-1,8-naphthalimide | 300702-27-6

• 英文名称: 4-bromo-N-(11-undecylferrocenyl)-1,8-naphthalimide
• 英文别名: N-(11-ferrocenylundecyl)-4-bromo-1,8-naphthalimide
• CAS: 300702-27-6
• 化学式: C₃₃H₃₆BrFeNO₂
• 分子量: 614.405
• InChiKey: SCQFMJINNCJNOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  哌啶 、 4-bromo-N-(11-undecylferrocenyl)-1,8-naphthalimide 以 neat (no solvent) 为溶剂， 以99%的产率得到4-piperidinyl-N-(11-undecylferrocenyl)-1,8-naphthalimide
  参考文献：
  名称：

  Tunable Donor−Acceptor Interactions in 4-Ene/Yne-Ferrocenyl and 4-Enamine Naphthalimides with Ferrocenyl Headgroups

  摘要：

  A series of 4-(X)-substituted naphthalimides (X = ethenylFc, ethynylFc, piperidinyl, ethenylpiperidinyl, ethenylpyrrolidinyl) with ferrocenyl headgroups (R = Fc(CH2)(n), n = 1, 5, 11) and analogous ethenylFc, ethynylFc, and ethynylFc(#) (Fc(#) = octamethylferrocenyl) compounds with a methyl headgroup have been investigated. These are the first 4-enamine-1,8-naphthalimides to be reported. Spectrochemical properties for all compounds are presented and the X-ray structures of 4-piperidinyl and 4-ethynylferrocenyl derivatives described. This series of donor-acceptor derivatives allows a correlation between the degree of internal charge separation, UV-vis and emission properties, and mediation by the organometallic redox couple. Charge separation increases in the order 4-amino much less than 4-C=C-amino congruent to4-Cequivalent toCFc congruent to 4-C=CFc < 4-Cequivalent toCFc(#). The unsaturated spacer is the key influence on both gimel(flu) and phi(f), but gimel(flu) is independent of the headgroup due to the imide node. In contrast, of shows a "distance" effect for the ferrocenyl headgroup, and as a result phif can be "tuned"; dyads with the Fc(CH2)(11) headgroup have phi(f) > 0.2. Solvatochromism data gives an excited state dipole of similar to8 D. An EPR study of radical anions provides a description of the SOMO. Through-space interaction between the ferrocenyl headgroup and the charge-separated excited state may account for some of the trends in EPR and of. In general, emission is decreased upon oxidation to the ferrocenium analogues.

  DOI：

  10.1021/om0304659
• 作为产物：
  描述：

  (11-aminoundecyl)ferrocene 、 4-溴-1,8-萘二甲酸酐 以 乙醇 为溶剂， 以75%的产率得到4-bromo-N-(11-undecylferrocenyl)-1,8-naphthalimide
  参考文献：
  名称：

  N-二茂铁基萘二甲酰亚胺：合成，结构和氧化还原化学

  摘要：

  的家庭Ñ -ferrocenyl-1,8-和Ñ -ferrocenyl -2,3-萘二甲酰亚胺和Ñ，Ñ -diferrocenyl -1,4,5,8- naphthaldiimide络合物已经准备由萘二甲酸酐或萘二甲酰亚胺阴离子与反应二茂铁胺。所述Ñ -ferrocenyl取代基是1,8-（FC，FCCH 2，FcCHMe，FC（CH 2）11），1,4,5,8-（FC，FCCH 2，FcCHMe，FC（CH 2）11），3- NO 2 -1,8-（FcCH 2，FcCHMe），4-NO 2 -1,8（Fc，FcCH 2，FcCHMe，Fc（CH 2）11，1,1'-BrFcCH 2），4-Br-1,8（FcCH 2，Fc（CH 2）11）和2,3（Fc，FcCH 2，FcCHMe，Fc（CH 2）11）。1,4,5,8-Fc和-FcCH 2衍生物会发生新型堆积聚集，并且分子内供体-受体电

  DOI：

  10.1021/om000352e