(E)-1-(7-(4-(benzo[d]thiazol-2-yl)styryl)-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)-3-(2-(9,10,16,17,18,19,21,22,23,24-decahydro-6H dibenzo[h,s][1,4,7,11,14,17]trioxatriazacycloicosin-20(7H)-yl)ethyl)thiourea | 1236254-41-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-(7-(4-(benzo[d]thiazol-2-yl)styryl)-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)-3-(2-(9,10,16,17,18,19,21,22,23,24-decahydro-6H dibenzo[h,s][1,4,7,11,14,17]trioxatriazacycloicosin-20(7H)-yl)ethyl)thiourea
• 英文别名: 1-[7-[(E)-2-[4-(1,3-benzothiazol-2-yl)phenyl]ethenyl]-9,9-bis[2-(2-ethoxyethoxy)ethyl]fluoren-2-yl]-3-[2-(2,5,8-trioxa-16,19,22-triazatricyclo[22.4.0.09,14]octacosa-1(28),9,11,13,24,26-hexaen-19-yl)ethyl]thiourea
• CAS: 1236254-41-3
• 化学式: C₆₅H₇₈N₆O₇S₂
• 分子量: 1119.5
• InChiKey: HAPURVUFWZAHKG-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  80
• 可旋转键数：
  21
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  锌 、 (E)-1-(7-(4-(benzo[d]thiazol-2-yl)styryl)-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)-3-(2-(9,10,16,17,18,19,21,22,23,24-decahydro-6H dibenzo[h,s][1,4,7,11,14,17]trioxatriazacycloicosin-20(7H)-yl)ethyl)thiourea 以 四氢呋喃 为溶剂， 生成 Zn(2+) (E)-1-(7-(4-(benzo[d]thiazol-2-yl)styryl)-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)-3-(2-(9,10,16,17,18,19,21,22,23,24-decahydro-6H dibenzo[h,s][1,4,7,11,14,17]trioxatriazacycloicosin-20(7H)-yl)ethyl)thiourea
  参考文献：
  名称：

  Fluorene-Based Metal-Ion Sensing Probe with High Sensitivity to Zn²⁺ and Efficient Two-Photon Absorption

  摘要：

  The photophysical, photochemical, two-photon absorption (2PA) and metal ion sensing properties of a new fluorene derivative (E)-1-(7-(4-(benzo[d]thiazol-2-yl)styryl)-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)-3-(2-(9,10,16,17,18,19,21,22,23,24-decahydro-6H dibenzo[h,s][1,4,7,11,14,17]trioxatriazacycloicosin-20(7H)-yl)ethyl)thiourea (1) were investigated in organic and aqueous media. High sensitivity and selectivity of 1 to Zn2+ in tetrahydrofuran and a water/acetonitrile mixture were shown by both absorption and fluorescence titration. The observed complexation processes corresponded to 1:1 stoichiometry with the range of binding constants similar to(2-3) x 10(5) M-1. The degenerate 2PA spectra of 1 and 1/Zn2+ complex were obtained in the 640-900 nm spectral range with the maximum values of two-photon action cross section for ligand/metal complex similar to(90-130) GM, using a standard two-photon induced fluorescence methodology under femtosecond excitation. The nature of the 2PA bands was analyzed by quantum chemical methods and a specific dependence on metal ion binding processes was shown. Ratiometric fluorescence detection (420/650 nm) provided a good dynamic range (10(-4) to 10(-6) M) for detecting Zn2+, which along with the good photostability and 2PA properties of probe 1 makes it a good candidate in two-photon fluorescence microscopy imaging and sensing of Zn ions.

  DOI：

  10.1021/jp104450m
• 作为产物：
  描述：

  2-(2,5,8-Trioxa-16,19,22-triazatricyclo[22.4.0.09,14]octacosa-1(28),9,11,13,24,26-hexaen-19-yl)ethanamine 、 2-(4-(2-(9,9-bis(2-(2-ethoxyethoxy)ethyl)-2-isothiocyisothiocyanato-fluoren-7-yl)vinyl)phenyl)benzothiazole 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以85%的产率得到(E)-1-(7-(4-(benzo[d]thiazol-2-yl)styryl)-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)-3-(2-(9,10,16,17,18,19,21,22,23,24-decahydro-6H dibenzo[h,s][1,4,7,11,14,17]trioxatriazacycloicosin-20(7H)-yl)ethyl)thiourea
  参考文献：
  名称：

  Fluorene-Based Metal-Ion Sensing Probe with High Sensitivity to Zn²⁺ and Efficient Two-Photon Absorption

  摘要：

  The photophysical, photochemical, two-photon absorption (2PA) and metal ion sensing properties of a new fluorene derivative (E)-1-(7-(4-(benzo[d]thiazol-2-yl)styryl)-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)-3-(2-(9,10,16,17,18,19,21,22,23,24-decahydro-6H dibenzo[h,s][1,4,7,11,14,17]trioxatriazacycloicosin-20(7H)-yl)ethyl)thiourea (1) were investigated in organic and aqueous media. High sensitivity and selectivity of 1 to Zn2+ in tetrahydrofuran and a water/acetonitrile mixture were shown by both absorption and fluorescence titration. The observed complexation processes corresponded to 1:1 stoichiometry with the range of binding constants similar to(2-3) x 10(5) M-1. The degenerate 2PA spectra of 1 and 1/Zn2+ complex were obtained in the 640-900 nm spectral range with the maximum values of two-photon action cross section for ligand/metal complex similar to(90-130) GM, using a standard two-photon induced fluorescence methodology under femtosecond excitation. The nature of the 2PA bands was analyzed by quantum chemical methods and a specific dependence on metal ion binding processes was shown. Ratiometric fluorescence detection (420/650 nm) provided a good dynamic range (10(-4) to 10(-6) M) for detecting Zn2+, which along with the good photostability and 2PA properties of probe 1 makes it a good candidate in two-photon fluorescence microscopy imaging and sensing of Zn ions.

  DOI：

  10.1021/jp104450m

文献信息

• Fluorene-Based Metal-Ion Sensing Probe with High Sensitivity to Zn²⁺ and Efficient Two-Photon Absorption
  作者：Kevin D. Belfield、Mykhailo V. Bondar、Andrew Frazer、Alma R. Morales、Oleksiy D. Kachkovsky、Ivan A. Mikhailov、Artëm E. Masunov、Olga V. Przhonska

  DOI：10.1021/jp104450m

  日期：2010.7.22

  The photophysical, photochemical, two-photon absorption (2PA) and metal ion sensing properties of a new fluorene derivative (E)-1-(7-(4-(benzo[d]thiazol-2-yl)styryl)-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)-3-(2-(9,10,16,17,18,19,21,22,23,24-decahydro-6H dibenzo[h,s][1,4,7,11,14,17]trioxatriazacycloicosin-20(7H)-yl)ethyl)thiourea (1) were investigated in organic and aqueous media. High sensitivity and selectivity of 1 to Zn2+ in tetrahydrofuran and a water/acetonitrile mixture were shown by both absorption and fluorescence titration. The observed complexation processes corresponded to 1:1 stoichiometry with the range of binding constants similar to(2-3) x 10(5) M-1. The degenerate 2PA spectra of 1 and 1/Zn2+ complex were obtained in the 640-900 nm spectral range with the maximum values of two-photon action cross section for ligand/metal complex similar to(90-130) GM, using a standard two-photon induced fluorescence methodology under femtosecond excitation. The nature of the 2PA bands was analyzed by quantum chemical methods and a specific dependence on metal ion binding processes was shown. Ratiometric fluorescence detection (420/650 nm) provided a good dynamic range (10(-4) to 10(-6) M) for detecting Zn2+, which along with the good photostability and 2PA properties of probe 1 makes it a good candidate in two-photon fluorescence microscopy imaging and sensing of Zn ions.