Organic Chemistry for Circular Economy

We investigate recovery and upcycling of valuable components from biomass using organic supramolecules as extractants and catalysts. In addition, our receptor molecules can bind either harmful or useful anions. The goal is to develop molecular level chemical applications for bio and circular economy.

Table of contents

Research group type
Research group
Core fields of research
Basic natural phenomena and mathematical thinking
Research areas
Circular Economy
Functional Molecules and Materials
Center of Expertise for Circular Economy
Sustainable society
Faculty
Faculty of Mathematics and Science
Department
Department of Chemistry

Research group description

The research combines organic supramolecular chemistry with strong expertise in chemical analytical techniques to create and investigate functional molecules, their non-covalent complexes and self-assembled structures. Mastering molecular design, synthesis, and molecular level interactions generates fundamental knowledge for many areas of chemistry and material sciences. In addition, we aim to create new applications for bio and circular economy and welcome collaboration with the private sector to bring these ideas alive.  Our research focuses on the following research areas.

1) Anion receptors that bind carboxylate and chloride anions

Carboxylate and chloride anions are ubiquitous in nature, thus their recognition has important applications. In the research project MAREXT: Macrocyclic Receptors for Selective Anion Extraction we investigated an and can bind anion inside or outside of the main cavity, and form ion-pair complexes with organic pyridinium and imidazolium cations. In addition, we synthesized an when the anion binds in the cavity, and remains in the kinetically stable closed state due to suitably rigid structure of the receptor. We also demonstrated that , which transport anions through lipid membrane. Artificial chloride transporters are envisioned as a potential cure for impaired chloride channel mediated diseases such as cystic fibrosis, or as anticancer agents.

2) Anion binding foldamers

Foldamers are synthetic oligomers that arrange in special shapes i.e. fold into defined conformation similarly to protein folding from an amino acid chain. Instead of amino acids, composition of foldamers can vary to almost any chemical building block. We have shown that anion binding especially with and arranges arylamide foldamers in a helical fold. In collaboration with Pihko group we investigate the effect of anion binding into the folding and catalytic activity of . The research project COCOA: Control of Catalyst Operation with Anions investigates anions as modulators for catalytic activity of foldamers, and conformational switching by anion binding in aqueous solvents.

3) Micelles and solid lipid nanoparticles containing supramolecular receptors

When supramolecular receptors have an amphiphilic structure (i.e.) polar and non-polar parts, they can self-assemble into micelles or form solid lipid nanoparticles. These nanoscale structures have wide range of applications in extraction and sensing, molecular transport, drug delivery, or in catalysis. We have shown that new types of supramolecular receptors such as and can form solid lipid nanoparticles. Currently we are investigating micelles and co-micelles of calixarene-type receptors for extraction of anions and as organocatalysts in biomass valorization.

4) Bioactive compounds from wild plants and biomass

In this new project we investigate extraction methods for recovery of bioactive compounds from biomass and prepare supramolecular complexes with bioactive molecules to improve the antiviral and antibacterial efficiency of plant extracts.

Research methods

  • Organic synthesis, especially calix[4]pyrroles, calix[n]arenes and resorcinarenes, and occasionally small organic molecules.
  • Organic analytical chemistry, including chromatographic techniques for separation, purification and characterization, NMR-spectroscopy for structural elucidation (1D, 2D, VT-NMR), other spectroscopic techniques including UV-VIS, IR and fluorescence spectroscopy.
  • X-ray crystallography of organic receptors and their supramolecular complexes with single crystal X-ray crystallography.
  • Dynamic light scattering (DLS) for nanoparticle size, monodispersity and zetapotential analysis.
  • NMR spectroscopy and isothermal titration calorimetry (ITC) for determination of binding constants and thermodynamic stability of supramolecular complexes.
  • Computational methods, i.e. density functional theory (DFT) calculations for supramolecular complexes (Gaussian, Turbomole, GPAW – in collaboration with computational groups)
  • We also utilize occasionally nanoscale imaging techniques (AFM, SEM, TEM), via in-house collaboration.
Laboratory work at synthesis laboratory with Combiflash
Combiflash at synthesis laboratory

Highlights and news

Visualization of calix[4]pyrrole chloride complex approaching liposome
The cis isomer of a calix[4]pyrrole bearing two urea-functionalized arms wraps around a chloride anion and shows 10 times higher transport activity into liposomes than the corresponding trans isomer, which can only use one arm for anion binding.
Anion responsive molecular switch based on calix[4]pyrrole receptor
Chloride, acetate and benzoate anions are kinetically trapped between the straps within the cavity of a doubly strapped calix[4]pyrrole receptor. The host switches conformation similarly to a Venus flytrap capturing an insect.

News archive

Publications

Publication
2024
Available through Open Access

European Journal of Organic Chemistry
Leino, Teppo
Noutsias, Dimitris
Helttunen, Kaisa
Moilanen, Jani
Tarkkonen, Eeki
Kalenius, Elina
Kiesilä, Anniina
Pihko, Petri M.
Publication
2023
Available through Open Access

Organic and Biomolecular Chemistry
Pamuła, Małgorzata
Bulatov, Evgeny
Martínez-Crespo, Luis
Kiesilä, Anniina
Naulapää, Julia
Kalenius, Elina
Helttunen, Kaisa
Publication
2023
Available through Open Access

Journal of Molecular Structure
Pamuła, Małgorzata
Bulatov, Evgeny
Helttunen, Kaisa
Publication
2022
Available through Open Access

European Journal of Organic Chemistry
Helttunen, Kaisa
Publication
2021
Available through Open Access

ACS Omega
Virtanen, Emilia J.
Perämäki, Siiri
Helttunen, Kaisa
Väisänen, Ari
Moilanen, Jani O.
Publication
2020
Available through Open Access

Chemistry : A European Journal
Pamuła, Małgorzata
Nissinen, Maija
Helttunen, Kaisa
Publication
2019
Available through Open Access

Chemistry : An Asian Journal
Helttunen, Kaisa
Annala, Riia
Suhonen, Aku
Iloniemi, Juho
Kalenius, Elina
Aragay, Gemma
Ballester, Pablo
Tuononen, Heikki
Nissinen, Maija
Publication
2017

CrystEngComm
Helttunen, Kaisa
Annala, Riia
Suhonen, Aku
Nauha, Elisa
Linnanto, Juha
Nissinen, Maija
Publication
2016
Available through Open Access

CrystEngComm
Helttunen, Kaisa
Nissinen, Maija
Publication
2016
Available through Open Access

Journal of Colloid and Interface Science
Helttunen, Kaisa
Galán, Albano
Ballester, Pablo
Bergenholtz, Johan
Nissinen, Maija
Publication
2015
Available through Open Access

Crystal Growth and Design
Suhonen, Aku
Morgan, Ian
Nauha, Elisa
Helttunen, Kaisa
Tuononen, Heikki
Nissinen, Maija
Publication
2015
Available through Open Access

CrystEngComm
Helttunen, Kaisa
Tero, Tiia-Riikka
Nissinen, Maija

External links

Group alumni and theses

Events

Research group

External members

Malgorzata Pamula

Doctoral Researcher
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