Synthesis and redox properties of π-conjugated 4,5-diazafluorene derivatives incorporating 9-cyanomethylene moiety as an electron acceptor

We have synthesized π-conjugated acceptor-type molecules 3a– d containing a cyanomethylene unit as the electron acceptor site and a 4,5-diazafluorene ligand for metal complexation. In the crystal, the planar 3a molecules stack along the b axis in the head-to-tail fashion. Compound 3a shows distincti...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2011-11, Vol.52 (44), p.5865-5868
Main Authors: Sako, Katsuya, Mugishima, Yasufumi, Iwanaga, Tetsuo, Toyota, Shinji, Takemura, Hiroyuki, Watanabe, Motonori, Shinmyozu, Teruo, Shiotsuka, Michito, Tatemitsu, Hitoshi
Format: Article
Language:English
Subjects:
4,5-Diazafluorene
Acceptor
Chemistry
Complexation
Coordination compounds
Crystals
Derivatives
Electrochemistry
Electrochromism
Exact sciences and technology
Free radicals chemistry
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Inorganic chemistry and origins of life
Knoevenagel condensation
Ligands
Microwave assisted synthesis
Miscellaneous (electroosmosis, electrophoresis, electrochromism, electrocrystallization, ...)
Organic chemistry
Preparations and properties
Radicals
Reactivity and mechanisms
Stacks
Tetrahedrons
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We have synthesized π-conjugated acceptor-type molecules 3a– d containing a cyanomethylene unit as the electron acceptor site and a 4,5-diazafluorene ligand for metal complexation. In the crystal, the planar 3a molecules stack along the b axis in the head-to-tail fashion. Compound 3a shows distinctive electrochromism and its three differently colored redox states (dianion ( 3 2−), anion radical ( 3 −), neutral ( 3)) exhibit remarkable stability.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.08.164