β‐Iminoenamine‐BF 2 Complexes: Aggregation‐Induced Emission and Pronounced Effects of Aliphatic Rings on Radiationless Deactivation

Abstract The synthesis, photophysical, and electrochemical attributes of a novel class of boron difluorides containing an aromatic‐fused alicyclic/hetero‐alicyclic ring built on a β‐iminoenamine chromophoric backbone are reported. The compounds displayed large Stokes shifts (86–121 nm), and were emi...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2012-11, Vol.7 (11), p.2670-2677
Main Authors: Perumal, Karthikeyan, Garg, Jai Anand, Blacque, Olivier, Saiganesh, Ramanathan, Kabilan, Senthamaraikannan, Balasubramanian, Kallupattu Kuppusamy, Venkatesan, Koushik
Format: Article
Language:English
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:Abstract The synthesis, photophysical, and electrochemical attributes of a novel class of boron difluorides containing an aromatic‐fused alicyclic/hetero‐alicyclic ring built on a β‐iminoenamine chromophoric backbone are reported. The compounds displayed large Stokes shifts (86–121 nm), and were emissive in the solid state. The quantum yields obtained in solution at room temperature were unusually lower by an order of magnitude compared to those in the solid state. Some of the tested compounds displayed aggregation‐induced emission (AIE). Single crystal XRD analyses revealed a lack of interplanar π–π interactions, which are presumed to be absent owing to non‐planarity of the alicyclic component in the molecule. For most of the studied compounds, time‐dependent DFT (TD‐DFT) calculations invariably reveal intramolecular charge transfer (π–π*) characteristics with the frontier orbitals concentrated on the boron–nitrogen heterocycle. The participation of boron and fluorine atoms was found to be negligible.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201200477