Novel quinoxalinone-based push-pull chromophores with highly sensitive emission and absorption properties towards...

Area of Science:

• Organic Chemistry
• Photophysics
• Computational Chemistry

Background:

• Push-pull chromophores are vital for optoelectronic applications.
• Quinoxalinone derivatives offer tunable photophysical properties.
• Understanding structure-property relationships is key for designing new materials.

Purpose of the Study:

• To synthesize and characterize novel quinoxalinone-based push-pull chromophores.
• To investigate the influence of electron-donor group positioning on photophysical properties.
• To elucidate the role of intramolecular charge-transfer (ICT) in emission efficiency.

Main Methods:

• Experimental photophysical measurements (absorption, emission, solvatochromism).
• Quantum chemical calculations (DFT, NTO analysis).
• Analysis of electronic density rearrangement using topological descriptors.

Main Results:

• Synthesized chromophores absorb and emit across the visible spectrum.
• Dimethylaminostyryl (DMAS) group position drastically affects absorption/emission intensities and solvatochromic behavior.
• No correlation found between DMAS conformation and photophysical properties.
• Quantum chemical methods successfully rationalized experimental spectral features, including Stokes shift.
• ICT was quantified but not identified as the primary factor for emission efficiency differences.

Conclusions:

• The position of the electron-donor group is a critical determinant of photophysical properties in these quinoxalinone chromophores.
• While ICT plays a role, other factors significantly influence emission efficiency in structurally similar push-pull systems.
• This work provides valuable insights for the rational design of novel chromophores with tailored optical properties.