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How polar are choline chloride-based deep eutectic solvents?

Ashish Pandey1, Rewa Rai, Mahi Pal

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Deep Eutectic Solvents (DESs) are promising green solvents. Their polarity, crucial for applications, was assessed using various probes, revealing structural influences on solvent properties.

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Area of Science:

  • Green Chemistry
  • Physical Chemistry
  • Materials Science

Background:

  • Developing cost-effective, low-toxicity green solvents is critical.
  • Deep Eutectic Solvents (DESs) offer advantages over traditional organic solvents and ionic liquids, including low volatility, non-flammability, biodegradability, and lower toxicity.
  • Assessing the polarity of DESs is essential for their adoption in industrial and academic applications.

Purpose of the Study:

  • To estimate the polarity of four common Deep Eutectic Solvents (DESs).
  • To investigate the influence of hydrogen bond donors on DES polarity.
  • To understand solute-solvent interactions within DESs using solvatochromic probes.

Main Methods:

  • Utilized solvatochromic optical spectroscopic responses from UV-Vis absorbance and molecular fluorescence probes.
  • Employed probes such as betaine dye, pyrene, pyrene-1-carboxaldehyde, ANS, TNS, PRODAN, coumarin-153, and Nile Red.
  • Investigated four DESs: ethaline, glyceline, reline, and maline, formed from choline chloride and different hydrogen bond donors (1,2-ethanediol, glycerol, urea, malonic acid) in a 1:2 molar ratio.

Main Results:

  • The four studied DESs exhibited fairly dipolar characteristics.
  • Ethaline and glyceline (alcohol-based H-bond donors) were found to be more dipolar than reline and maline, according to photoinduced charge-transfer probes.
  • The pyrene polarity scale indicated reline (urea-based) as significantly more dipolar, while pyrene-1-carboxaldehyde suggested maline as the most dipolar.
  • The molecular structure of the hydrogen bond donor strongly influences the DES's dipolarity.

Conclusions:

  • The polarity of DESs is effectively assessed using solvatochromic probes.
  • The choice of hydrogen bond donor is a key factor in determining the effective polarity and microenvironment of a DES.
  • Specific solute-solvent interactions, including hydrogen bonding, play a significant role in the behavior of solvatochromic probes within DESs.