octasodium salt of 5,11,17,23,29,35,41,47-octasulfonatocalix<8>arene | 105190-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: octasodium salt of 5,11,17,23,29,35,41,47-octasulfonatocalix<8>arene
• 英文别名: calix[8]arene-p-octasulfonic acid sodium salt；p-sulfonato-calix[8]arene sodium；sodium p-sulfonatocalix[8]arene；sulfocalix[8]arene；octasodium salt of 5,11,17,23,29,35,41,47-octasulfonatocalix[8]arene
• CAS: 105190-41-8；114324-27-5
• 化学式: C₅₆H₄₀O₃₂S₈*8Na
• 分子量: 1665.36
• InChiKey: WFLOUYNSJAZRKT-UHFFFAOYSA-F

计算性质

• 辛醇/水分配系数(LogP)：
  -1.39
• 重原子数：
  97.0
• 可旋转键数：
  8.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  619.44
• 氢给体数：
  8.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-(dimethylamino)styryl)-1-methylpyridinium iodide 、 octasodium salt of 5,11,17,23,29,35,41,47-octasulfonatocalix<8>arene 以 acetate buffer 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  水溶性杯芳烃与几种芪染料的分子缔合及其在简便测定阳离子表面活性剂浓度中的应用

  摘要：

  已通过分光光度法和 1H NMR 方法研究了水溶性对磺基杯 [n] 芳烃（1n；n = 4、6 和 8）与几种二苯乙烯染料 (D) 的分子缔合。发现 1n 以 1:1 的化学计量与 D 反应，例如 4-[(4-二甲基氨基)苯乙烯基]-1-甲基吡啶鎓 (St–4Me)、2-[(4-二甲基氨基)苯乙烯基]-1-甲基吡啶鎓(St-2Me) 和 2-[(4-二甲氨基) 苯乙烯基]-1-乙基吡啶鎓 (St-2Et) 碘化物形成它们的复合物 (1nD)。18-复合物的表观缔合常数比 14-和 16-复合物的表观缔合常数大约 10 倍。CPK 分子模型的检查和分光光度法研究表明，14 种复合物 D 主要与其 1-甲基-或 1-乙基吡啶鎓基团复合，而 16 种复合物 D 与其吡啶鎓环或质子化二甲氨基基团以相似的概率复合，

  DOI：

  10.1246/bcsj.70.2131
• 作为产物：
  描述：

  4-叔丁基杯[8]芳烃 在 硫酸 、 sodium carbonate 作用下， 以 水 为溶剂， 以63%的产率得到octasodium salt of 5,11,17,23,29,35,41,47-octasulfonatocalix<8>arene
  参考文献：
  名称：

  通过主客体与对磺基杯[n]芳烃络合来稳定花青素颜色

  摘要：

  酸性和阳离子形式的黄酮类化合物会使水溶液变色，而在微酸性或中性条件下，它们通常会变色。水溶性对磺基杯[n]芳烃 (SCn) 大环化合物和黄花阳离子物质之间的选择性主客体络合可以增加有色形式的稳定性，扩大其在 pH 范围内的范围。SCn 与阳离子（酸）和中性碱性形式的黄鎓基化合物之间的缔合常数是通过在不同 pH 值下通过 UV-Vis 主客体滴定确定的。发现宿主对合成生色团的亲和力高于对天然花青素 (Oenin) 的亲和力。SC4的用于合成flavylium较高亲和力是通过确认1H NMR 显示黄鎓苯环与主体腔的优先相互作用。与其合成对应物相比，花青素中的黄芪取代模式似乎限制了客体在宿主结合口袋中的包含。在这种情况下，观察到八聚体 (SC8) 具有更高的亲和力，这可能是由于其更大的空腔和更多数量的带负电荷的磺酸盐基团。

  DOI：

  10.3390/molecules26175389

文献信息

• NMR determination of association constants for calixarene complexes. Evidence for the formation of a 1:2 complex with calix[8]arene
  作者：Seiji. Shinkai、Koji. Araki、Osamu. Manabe

  DOI：10.1021/ja00229a046

  日期：1988.10

  Formation de composes d'inclusion entre le chlorure de N,N,N-trimethyl anilinium et des p-sulfonato-calix [n] arenes ou n=2, 4 ou 8

  N,N,N-trimethyl anilinium et des p-sulfonato-calix [n] 芳烃 ou n=2, 4 ou 8
• Intermolecular Complexation Between p-Sulfonated Calix[4,6,8]arene Sodium and Neutral Red
  作者：M. Chen、G. W. Diao

  DOI：10.1007/s10953-011-9660-z

  日期：2011.3

  The inclusion complexation behavior of the dye guest molecule neutral red with three kinds of water-soluble p-sulfonated calix[n]arene sodium (n=4,6,8) was investigated. p-Sulfonated calix[4,6,8]arene sodium (pSC4, pSC6, pSC8) can react with neutral red to form inclusion complexes, which were confirmed by UV-vis absorption and fluorescence spectroscopy. Fluorescence spectroscopy experiments were performed in pH=4.6 acetic buffer solutions at 25 °C to calculate the stability constants (K S) for the stoichiometric 1:1 inclusion complexes of pSC4, pSC6 and pSC8 with neutral red. The thermodynamic parameters for the inclusion complexes were determined through a van’t Hoff analysis. Formation of the inclusion complexes of pSC4, pSC6 and pSC8 with neutral red was driven by favorable enthalpic changes with their accompanying negative entropy changes. The complex stability constants monotonically increased with the number of phenolic units in the calixarene ring, which was attributed mainly to electrostatic interactions and hydrogen bonding, rather than to the cavity size.

  研究了染料客体分子中性红与三种水溶性对磺化钙[n]炔钠（n=4,6,8）的包合络合行为。对磺化钙[4,6,8]炔钠（pSC4, pSC6, pSC8）能与中性红反应形成包合络合物，并通过紫外-可见吸收和荧光光谱证实了这一点。荧光光谱实验是在 25 °C、pH=4.6 的乙酸缓冲溶液中进行的，目的是计算 pSC4、pSC6 和 pSC8 与中性红按 1:1 的比例形成的包合物的稳定常数（K S）。包合物的热力学参数是通过范特霍夫分析确定的。pSC4、pSC6 和 pSC8 与中性红的包合复合物的形成是由有利的焓变和伴随的负熵变驱动的。络合物的稳定性常数随萼烯环中酚类单元数量的增加而单调增加，这主要归因于静电相互作用和氢键，而非空腔大小。
• Aqueous on/off fluorescent switches based on systems of quinoline / quinoline-macrocycle
  作者：Matías E. Carranza、Hugo M. Elero、Alicia V. Veglia

  DOI：10.1016/j.jphotochem.2019.112253

  日期：2020.3

  spectrophotometric and the spectrofluorimetric properties of Quinoline (QUI) by the addition of water soluble macrocycles with different characteristics such as cyclodextrins (CD; α, β, hydroxypropyl-β, methyl-β and γ) and sulfonate calixarenes (SCAn, n = 6 and 8) were analyzed at acidic and neutral pH at 25.0 °C. Spectral changes were observed for the basic form of QUI. Small decreases of absorbance were

  在分光光度法和变化将喹啉（的荧光光谱特性QUI通过加入具有不同特性的水溶性的大环化合物），例如环糊精（CD ;α，β，羟丙基β，甲基-β和γ）和磺酸杯芳烃（扫描，在25.0°C的酸性和中性pH下分析n = 6和8）。观察到基本形式的QUI的光谱变化。吸光度的小幅下降表明QUI与大环化合物之间存在相互作用。在QUI- βCD和QUI-γCD的情况下确定缔合常数。在所有情况下，QUI的荧光在大环存在下淬灭。斯特恩-沃尔默常数（数值ķ Q / M -1）分别为（54.030±0.001）和（57.050±0.001），用于βCD和γCD和（3.8±0.1）×10 4和（2.40±0.06）×10 4用于SCA6和SCA8。这些值解释为缔合常数（ķ阿形成在由于荧光淬灭基态非荧光复合的）评价为静态的。CD大环产生的荧光异常猝灭和K A值的高差异对于CD和SCA的解释是通过在所研究的系统中作为开/关的系统中不同类型的特定交互作用来解释的。
• <i>P</i>-Sulfonatocalix[8]arene coordinates sodium cations and forms host-guest complex with berberine: insight from crystal structure
  作者：Kateryna Kravets、Mykola Kravets、Karolina Kędra、Oksana Danylyuk

  DOI：10.1080/10610278.2022.2161901

  日期：2021.12.2

  state assemblies with both inorganic and organic cations. Upon coordination of sodium cations to all sulphonate groups of the macrocycle the 3-D coordination polymer is formed. The C8S adopts circular pleated loop conformation and macrocyclic molecules are assembled into stacks stapled by coordination to multiple sodium cations. The arrangement of the metallo-supramolecular assembly is pseudo-hexagonal

  摘要 在本文中，我们扩大了大而灵活的大环主体对磺酸根[8]芳烃 ( C8S ) 在构建具有无机和有机阳离子的固态组装体中的应用。在钠阳离子与大环的所有磺酸盐基团配位后，形成 3-D 配位聚合物。 采用圆形褶皱环构象，大环分子通过与多个钠阳离子的配位组装成堆叠。金属超分子组装体的排列是假的-六角形。在有机阳离子小檗碱存在下，有利于主客体复合物。大环采用没有实质性内腔的构象，其中两个苯磺酸基团向分子中心倾斜。一个宿主将八个小檗碱客体结合在大环分子表面的凹槽和裂缝中。 是固态小檗碱的合适宿主，这种结晶驱动的主客体络合具有扩展小檗碱晶型库的潜力。
• New water-soluble host calixarenes bearing chiral substituents
  作者：Takashi Arimura、Hirosuke Kawabata、Tsutomu Matsuda、Tsuyoshi Muramatsu、Hiroshi Satoh、Kazunari Fujio、Osamu Manabe、Seiji Shinkai

  DOI：10.1021/jo00001a057

  日期：1991.1

  Chiral p-sulfonatocalix[n]arenes (n = 4, 6, and 8) bearing (S)-2-methylbutoxy groups (1(n)) have been synthesized. 1(n = 4) gave a simple, positive CD band, whereas 1(n = 6) and 1(n = 8) gave split CD bands characteristic of an exciton coupling at 1L(a) region. The sign (positive first Cotton effect and negative second Cotton effect) indicates that the chirality of excitons in these calixarenes is arranged in a clockwise direction. The difference between 1(n = 4) and the larger calixarenes 1(n = 6) and 1(n = 8) is accounted for by the difference in the ring rigidity: that is, 1(n = 6) nad 1(n = 8) are flexible enough to allow interactions of excitons in the excited state, whereas 1(n = 4) is too rigid to allow the interactions. On the addition of guest molecules (aliphatic alcohols) the CD band of 1(n = 4) was scarcely changed, whereas those of 1(n = 6) and 1(n = 8) were weakened. This result, together with the H-1 NMR data, suggests that the conformational fluctuation in 1(n = 6) and 1(n = 8) is considerably suppressed upon inclusion of these guest molecules. In the presence of 1(n = 6) or 1(n = 8) ICD bands were also observed for certain dye molecules (e.g., 4-cyano-4'-(diethylamino)azobenzene and 4-nitro-4'-(diethylamino)azobenzene). Careful comparison of the ICD spectra with the absorption spectra established that the calixarene complexes having 2:1 guest/calixarene stoichiometry are ICD-active whereas those having 1:1 guest/calixarene stoichiometry are ICD-silent. Interestingly, the sign of the Cotton effect showed that 4-cyano-4'-(diethylamino)azobenzene included in 1(n = 6) gives a counterclockwise exciton coupling, whereas that included in 1(n = 8) gives a clockwise exciton coupling. Thus, the present study demonstrates that the CD spectral technique is very useful to obtain insights into calixarene conformations and calixarene complexation properties.