3-(3-thienyl)-4,4-di(3-thienyl)-8-(2-thienyl)-4-bora-3a,4a-diaza-s-indacene | 1000778-99-3

• 英文名称: 3-(3-thienyl)-4,4-di(3-thienyl)-8-(2-thienyl)-4-bora-3a,4a-diaza-s-indacene
• CAS: 1000778-99-3
• 化学式: C₂₅H₁₇BN₂S₄
• 分子量: 484.498
• InChiKey: WIIDYYLJMYSOBB-UHFFFAOYSA-N

计算性质

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

反应信息

• 作为产物：
  描述：

  3-thienyl lithium 、 以 四氢呋喃 为溶剂， 反应 0.17h， 以11%的产率得到3-(3-thienyl)-4,4-di(3-thienyl)-8-(2-thienyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Boron-dipyrrin compounds comprising thienyl groups, preparation method thereof and chemosensor comprising the same

  摘要：

  本公开了（i）具有噻吩基团的硼-二吡咯烯化合物，（ii）其制备方法和（iii）包含具有噻吩基团的硼-二吡咯烯化合物的化学传感器。更具体地，本发明提供了具有噻吩基团、呋喃（OC4H3）基团或硒代基（SeC4H3）基团的硼-二吡咯烯化合物，其由以下式（1）表示，以及其制备方法和包含上述具有噻吩基团的硼-二吡咯烯化合物的化学传感器，其特征在于该化学传感器由于硼-二吡咯烯化合物与金属离子（包括但不限于Cu2+和Hg2+）的反应而表现出颜色和荧光特性的变化：3-（R）-4,4-双（R）-8-（R）-4-硼-3a,4a-二氮-茚烯  式（1）其中R是从2-噻吩基团和3-噻吩基团中选取的任一基团。

  公开号：

  US20090203923A1

文献信息

• Cu²⁺ Colorimetric Sensing and Fluorescence Enhancement and Hg²⁺ Fluorescence Diminution in “Scorpionate”-like Tetrathienyl-Substituted Boron−Dipyrrins
  作者：Shin Hei Choi、Keliang Pang、Kibong Kim、David G. Churchill

  DOI：10.1021/ic701101j

  日期：2007.12.1

  Four novel tetrathienyl-substituted boron-dipyrrin-type (BODIPY-type) complexes, 3-(R')-4+di(R')-8-R-4-bora3a,4a-diaza-s-indacene (4a, R = 2-T, R' = 2-T; 4b, R = 3-T, R' = 2-T; 5a, R = 2-T, R' = 3-T; 5b, R = 3-T, R' = 3-T; T = thienyl) have been prepared and fully characterized to explore patterns of stoichiometric Mn+ recognition in solution. Treatment of the respective parent BF2 dipyrrin with 2- or 3-thienyllithium gave the unexpected asymmetric tetrathienyl-substituted products in 8.5-35% yield. Compounds 4a and 4b bear a neutral "scorpionate"like [SSS] tridentate binding pocket. Extensive NMR and UV-vis spectroscopic studies were performed on 4a-5b; 5a, 4b, and 5b were structurally characterized. The Phi(F) values for 4a-5b all decrease compared to the BF2-containing parent molecules (0.00058, 0.012, 0.00090, and 0.0051, respectively), with lambda(abs,max) values (is an element of, M-1 cm(-1)) of 563 (44 000), 553 (29 000), 539 (33 000), and 531 (44 000) nm, respectively, and Stokes' shifts of 25-36 nm. Upon treatment with metal ion (Ca2+, CS+, Mn2+, CO2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, Pb2+) perchlorate salts, the solution of 4b undergoes rapid pink-to-clear switch-off behavior upon Cu2+ addition (10 mu M scale) with smaller effects seen for 4a. Further, there were 2- to 19-fold Cu2+ fluorescence enhancements for these ligands. Cu2+ and Hg2+-L (L = 4a-5b) binding was modeled, and response patterns for Mn+-L 1:1 molar solutions upon Cu2+ addition were measured. Upon treatment with Hg2+, all ligand solutions show a significant fluorescence decrease accompanied by minor absorption increases. The UV-vis spectroscopic detection limit for Cu2+ and Hg2+ is similar to 270 ppb and similar to 1.7 ppm, respectively; the naked eye detection limit for Cu2+ with 4b (1.0 x 10(-5) M) is similar to 23 mu M. DFT calculations gave HOMO-LUMO gaps of 478 (4a), 462 (4b), 448 (5a), and 442 nm (5b). Molecular orbital diagrams for 4a-5b revealed that the HOMO and LUMO electron density is distributed onto the 3-position-thienyl group and to a lesser degree the B(thienyl)(2) moiety.