Quinone-Bodipy H-bonding interaction over π-stacking in toluene
Animesh Karmakar1, Soumyaditya Mula, Kalyan Ghosh
1Department of Chemistry, Dr Bhupendranath Dutta Smriti Mahavidyalaya, Burdwan-713407, India. tanchem_bu@yahoo.co.in.
Summary
Quinone compounds effectively form hydrogen bonds with a Bodipy dye in toluene. Unlike fullerenes, these quinones create unique isoemissive complexes, confirmed by NMR and computational studies.
Area of Science:
- Supramolecular Chemistry
- Photophysics
- Organic Chemistry
Background:
- Bodipy dyes are versatile fluorescent molecules with applications in sensing and imaging.
- Hydrogen bonding plays a crucial role in molecular recognition and self-assembly.
- Quinones and fullerenes are known electron acceptors with distinct interaction profiles.
Purpose of the Study:
- To investigate the hydrogen bonding interactions between quinone compounds and a meso-phenol Bodipy dye.
- To compare the interaction behavior of quinones with that of fullerenes with the Bodipy dye.
- To elucidate the ground and excited state properties of the resulting complexes.
Main Methods:
- UV-Vis absorption and fluorescence spectroscopy were used to study the interactions.
- Isosbestic points and isoemissive behavior were analyzed to understand complex formation.
- (1)H Nuclear Magnetic Resonance ((1)H NMR) spectroscopy provided structural insights.
- Monte Carlo global minima searching was employed for computational validation.
Main Results:
- Quinone type compounds (o-chloranil, p-chloranil, and DDQ) exhibit strong H-bonding with the Bodipy dye (1) in toluene.
- Spectroscopic evidence confirmed isosbestic absorption with both quinones and fullerenes.
- Crucially, only quinones formed isoemissive complexes with dye 1, indicating specific binding modes.
- NMR and computational studies supported the observed H-bonding interactions and complex structures.
Conclusions:
- Quinones are effective H-bonding partners for meso-phenol Bodipy dyes, influencing their photophysical properties.
- The formation of isoemissive complexes distinguishes quinone interactions from those of fullerenes.
- This study highlights the potential of quinone-Bodipy systems for developing novel supramolecular assemblies and sensors.
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