Cargo-towing Highly enantioselective Electro-pumps: unconventional asymmetrIc Readout and transmission of chiral information

Project Information

CHEIR

Grant agreement ID: 101040798

DOI

10.3030/101040798

EC signature date 9 February 2022

Start date 1 June 2022

End date 31 May 2027

Funded under

• European Research Council (ERC)

Total cost

€ 1 492 004,00

EU contribution

€ 1 492 004,00

Coordinated by

UNIVERSITA DEGLI STUDI DI MILANO
Italy

Periodic Reporting for period 1 - CHEIR (Cargo-towing Highly enantioselective Electro-pumps: unconventional asymmetrIc Readout and transmission of chiral information)

Reporting period: 2022-06-01 to 2024-11-30

Summary of the context and overall objectives of the project

The project “CHEIR” aims to develop chiral cargo delivery electro-pumps to be employed in biological transport for ex-situ applications. Essentially, the PI wants to design a groundbreaking system that serves as a proof of concept for its category because it involves three different “types” of chirality: 1. axial chirality of the selector, 2. helical chirality induced by the shape of the electro-pump, 3. central chirality of the cargos stemming from stereocenters. The combination of four main ingredients, 1.electric field and 2. magnetic field (externally applied), 3. electrical conductivity and 4. selector enantiodiscrimination capability (intrinsic feature of the object), makes these innovative miniaturized bipolar soft pumps perfect candidates for a multipurpose asymmetric detection that leads to load, transport and deliver the desired chiral analytes.
In the “CHEIR” project the architecture of the cargo and delivery system has been designed as a “helical coaxial tubular” conducting oligomer/polymer to combine electro-pumping (cave tube) and mobility (screw- like shape) capability. The shell of the helical tube will be constituted by a conducting polymer, like polypyrrole, endowed with good electromechanical feature (pumping effect), and the internal surface by inherently chiral oligothiophenes (chiral recognition of the cargo). This soft polymeric object will be triggered and controlled exploiting an attractive combination of electric and magnetic fields, both finely tuned for loading and unloading of desired species (electric field) and for moving (magnetic one).

Work performed from the beginning of the project to the end of the period covered by the report and main results achieved so far

The project's five most significant achievements are as follows:

Development of the Wireless Tubular Devices: The successful design and synthesis of dual-layered tubular devices that leverage bipolar electrochemistry for chiral resolution. These devices represent a significant technological advancement.

High-Impact Publications: The findings were published in high-impact peer-reviewed journals such as CHEM and Analytical Chemistry, which have significantly enhanced the visibility and impact of the research.

Achievement of High Enantiomeric Purity: The project consistently achieved high enantiomeric excess (ee) values exceeding 90%, demonstrating the system's efficiency and effectiveness in chiral separation.

Interdisciplinary Collaboration: The project fostered collaboration between experts in various fields, leading to innovative solutions that combined electrochemistry, materials science, and pharmaceutical chemistry.

Versatility in Chiral Separation: The system's ability to handle a wide range of chiral analytes, including complex mixtures, highlights its robustness and potential for broad applications in pharmaceutical analysis.

Progress beyond the state of the art and expected potential impact (including the socio-economic impact and the wider societal implications of the project so far)

The project achieved several breakthroughs and advancements beyond the current state-of-the-art in chiral resolution:

Innovative Use of Bipolar Electrochemistry: The application of bipolar electrochemistry in chiral resolution represents a novel approach that has not been widely explored in the field. This technique provides a new mechanism for inducing fluid movement and enhancing the separation process.

High Efficiency and Purity: Achieving enantiomeric excess (ee) values exceeding 90% with a simple, cost-effective system was an unexpected and significant breakthrough. This level of efficiency and purity sets a new standard in the field of chiral separation.

Unplanned Discoveries: The strong diastereomeric interactions observed in the tubular devices were beyond initial expectations. These interactions provided new insights into the mechanisms of chiral separation and highlighted the potential for further optimization and improvement of the system.