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双(亚甲基)双(5-溴-2-羟基水杨酰腙)的多功能应用:从金属传感到A3偶联反应的环境催化

A multifunctional use of bis(methylene)bis(5-bromo-2-hydroxyl salicyloylhydrazone): from metal sensing to ambient catalysis of A3 coupling reactions.

作者信息

Peewasan Krisana, Merkel Marcel P, Fuhr Olaf, Anson Christopher E, Powell Annie K

机构信息

Institute of Inorganic Chemistry, Karlsruhe Institute of Technology Engesserstrasse 15 76131 Karlsruhe Germany

Institute of Nanotechnology, Karlsruhe Institute of Technology Campus North Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen Karlsruhe Germany.

出版信息

RSC Adv. 2020 Nov 9;10(67):40739-40744. doi: 10.1039/d0ra07687b.

DOI:10.1039/d0ra07687b
PMID:35519231
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9057725/
Abstract

The potential use of bis(methylene)bis(5-bromo-2-hydroxylsalicyloylhydrazone) as a multifunctional fluorescence sensor for Cu, Ni, Co and Fe ions was investigated. The optical behaviour shows an increase in an absorption band at 408 nm which can be ascribed to the d-d transition (UV-vis) of the metal ions and a concomitant decrease in fluorescence intensity at 507 nm. The crystallographic analysis shows the binding site of the sensor to two Cu ions and confirms the stoichiometry of 1 : 2 (ligand to metal) which is in good agreement with a Job plot analysis. Furthermore the Cu-complex catalyses A3 coupling reactions at 1 mol% catalytic loading; chiral propargylamine derivatives were obtained in high yield after 24 h reaction time under ambient conditions.

摘要

研究了双(亚甲基)双(5-溴-2-羟基水杨酰腙)作为铜、镍、钴和铁离子多功能荧光传感器的潜在用途。光学行为表明,408nm处吸收带增加,这可归因于金属离子的d-d跃迁(紫外可见),同时507nm处荧光强度降低。晶体学分析表明传感器与两个铜离子的结合位点,并证实了1:2(配体与金属)的化学计量比,这与Job曲线分析结果良好吻合。此外,铜配合物在1mol%催化负载量下催化A3偶联反应;在环境条件下反应24小时后,以高产率获得了手性炔丙胺衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/f780464a108f/d0ra07687b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/54ebbc344a21/d0ra07687b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/090d00dcabec/d0ra07687b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/0accd2a3fe07/d0ra07687b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/07443f42fa90/d0ra07687b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/0212dd031435/d0ra07687b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/f780464a108f/d0ra07687b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/54ebbc344a21/d0ra07687b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/090d00dcabec/d0ra07687b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/0accd2a3fe07/d0ra07687b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/07443f42fa90/d0ra07687b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/0212dd031435/d0ra07687b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d52a/9057725/f780464a108f/d0ra07687b-f5.jpg

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