4 years ago

Synthesis and Properties of Salicylaldehydes Fine-Tuned by Modular Assembly using “Plug-and-Socket”-Type Extendibility

Synthesis and Properties of Salicylaldehydes Fine-Tuned by Modular Assembly using “Plug-and-Socket”-Type Extendibility
Yoshikazu Suzuki, Qian-Wen Shen, Toshiki Mutai, Isao Yoshikawa, Hirohiko Houjou
A salicylaldehyde derivative bearing four pyridine arms, 3,5-bis(N,N-bis(2-pyridylmethyl)aminomethyl)-2,4-dihydroxybenzaldehyde (Hbpsal) as a “socket”, was prepared and used to derive a series of zinc complexes with various extra anions “plugged” into their vacant site. The crystal structure and 1H NMR spectra were noticeably influenced by the extra anions, allowing fine-tuning of the properties by “plug-and-socket”-type modification. Similar to unsubstituted salicylaldehyde, the zinc complexes reacted with primary amines to afford Schiff-base compounds. Because of the potential chirality around the coordination sphere, reaction with a chiral amine resulted in an equilibrium system between diastereomers, the potential of which as chiral sources tunable by the extra anions is discussed. Some of the complexes were further converted into zinc- or nickel-salphen (=N,N-bis(salicylidene)-1,2-phenylenediamine) complexes. The electrochemical properties of the nickel complex were slightly modified by the extra anions, whereas the photophysical properties of the zinc complex appeared unchanged. Peripherals: Salicylaldehyde provided with a “socket”-shaped zinc complex into which various extra anions can be “plugged” was developed. The prochirality around the coordination sphere demonstrated its potential as a chiral source tunable by the extra anions. The salicylaldehyde was derived to Schiff-base complexes, the electrochemistry of which was significantly influenced by the anions.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701141

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.