Mechanochemistry: Microscopic and Macroscopic Aspects

Beilstein Organic Chemistry Symposium 2018

13 – 15 November, 2018
Hotel Jagdschloss Niederwald, Ruedesheim, Germany

 

Scientific Program:

José G. Hernández / RWTH Aachen University, Germany

 

Summary

The Beilstein Organic Chemistry Symposium “Mechanochemistry: Microscopic and Macroscopic Aspects”, took place from November 13th to 15th, 2018 at the Jagdschloss Hotel in Rüdesheim, Germany. In this magical venue, over forty worldwide experts on the field of mechanochemistry gathered together to disrupt the silence and calmness of this beautiful site with their mechanical energy. Put into numbers, this symposium consisted of twenty-two lectures given by international invited speakers, together with eighteen poster presentations showing recent breakthroughs in mechanochemistry.

On the first day, Dr. Martin G. Hicks opened the symposium by sharing the vision and philosophy of the Beilstein-Institut and by highlighting the appropriateness of open science in current times. Next, Dr. José G. Hernández (RWTH Aachen University) introduced the scientific program of the symposium emphasizing the importance of bringing together leading experts under one roof to understand the broadness and richness of mechanochemistry. Indeed, during the first scientific session of the symposium Prof. Stuart L. James (Queen’s University Belfast) showed the wideness of mechanochemistry, the sustainability aspects of mechanochemical reactions and the opportunities for commercialization of mechanochemically made products. Then, an energetic presentation by Prof. Tomislav Friščić (McGill University) delved into the thermodynamics aspects of mechanochemical reactions and the advantages of in situ monitoring of ball milling transformations. After a vivid coffee break, Prof. Stephen Craig (Duke University) introduced the microscopic aspects of mechanochemistry by showing the usefulness of introducing force-reactive functional moieties (mechanophores) in polymers to develop mechanically responsive materials and devices. Complementary, Prof. Martin K. Beyer (University of Innsbruck) demonstrated how single-molecule force spectroscopic techniques enable the transduction of mechanical forces with high directionality and the possibility to measure the mechanical loads required to mechanochemically rupturing covalent bonds.

The Tuesday’s afternoon session began with a presentation by Prof. Frédéric Lamaty (University of Montpellier), who showed the importance of ball milling techniques to develop mechanochemical organic and organometallic syntheses, with implications in chemistry and biology. Then, Dr. Joseph S. Vyle (Queen’s University Belfast) took all the attendees through a journey from the early days to the present to highlight the vital role of mechanochemistry in developing nucleic acid chemistry. The second part of the afternoon was dedicated to presentations focused on synthetic organic mechanochemistry by Prof. Guan-Wu Wang (University of Science and Technology of China) and Prof. José Carlos Menendez (Complutense University of Madrid), who demonstrated the power of mechanochemistry to build supramolecular assemblies and to develop diversity-oriented synthesis based on multicomponent reactions, respectively.

After an entertaining first day of oral presentations, the symposium was complemented by the first of two excellent poster sessions, which provided additional opportunities for interaction and scientific discussion between all participants.

The second day of the meeting began with a comprehensive talk by Prof. Carsten Bolm (RWTH Aachen University) describing the advantages of mechanochemistry in the field of catalysis. Specifically, a palette of solvent-free metal-catalyzed C–H functionalizations were presented. The morning session continued with an enjoyable lecture by Prof. James Mack (University of Cincinnati) entitled “Developing Selective Reactions under Mechanochemical Conditions”, in which the importance of milling parameters (e.g., frequency) and temperature control for the outcome of mechanochemical reactions were discussed. Next, Prof. Dominik Marx (Ruhr University Bochum) brought along his expertise on computational chemistry to provide a molecular understanding of the mechanochemical cycloreversion of triazoles in the context of covalent mechanochemistry. The final talk of the Wednesday’s morning session was given by Prof. Sergi Garcia-Manyes (King’s College London), who covered the microscopic aspects of mechanochemistry by using single-molecule force clamp spectroscopy. Particularly interesting were the findings that showed how tensile forces could change the free-energy surface of chemical transformations, leading to the formation of otherwise thermodynamically unfavored products.

Following an exquisite lunch, the afternoon session began with a presentation by Prof. Evelina Colacino (University of Montpellier and Institute Charles Gerhardt of Montpellier) who described systematic experimental work towards the mechanosynthesis of hydantoin derivatives. Similarly, during this presentation, an alternative approach to high-throughput mechanochemical synthesis was introduced. The second talk of the afternoon was given by Dr. José G. Hernández (RWTH Aachen University) who demonstrated that although most mechanochemical reactions carried out by ball milling are associated with transformations of solids and liquids; mechanochemical activation of gaseous reactants is equally feasible and advantageous. After a coffee break, the attendees returned to listen to Dr. Olena Vozniuk (Max Planck Institute for Coal Research), who provided an elaborate overview of the mechanosynthesis of metal hydrides, biomass conversion by mechanocatalysis, and demonstrated the value of continuous heterogeneously catalyzed gas-phase reactions using high-technology grinding equipment. Finally, Dr. Lars Borchardt (TU Dresden) closed the second day of the symposium demonstrating the importance of porous materials and in particular, how ball milling techniques can be applied to improve and develop their synthesis.

Once again, the second poster session of the meeting kept all the participants entertained with great presentations, which expanded on the use of atomic-force microscopy, ball milling and sonication techniques to carry out mechanochemical reactions. Then, after a series of fruitful scientific discussions the day ended with all the participants enjoying dinner together.

The third and last day of the symposium commenced with a presentation by Dr. Deborah E. Crawford (Queen’s University Belfast). This morning talk highlighted not only the value of ball milling techniques to carry out mechanochemical reactions but also exemplified the advantages of twin-screw extrusion (TSE) for the scaling up synthesis of metal organic frameworks (MOFs), deep eutectic solvents (DESs) and organic reactions. Complementary, Dr. Sandra Breitung-Faes (Braunschweig University of Technology Germany), gave interesting inputs for the coupling between experimental work and discrete element simulations (DEM), predicting models that help to optimize the grinding process, the scaling up and the ball mills’ design.

Next, Prof. Krunoslav Užarević (Ruder Bošković Institute) explained how the development of continuous monitoring methods for mechanochemical reactions has enabled understanding chemical mechanisms and kinetics during solid-state transformations. In particular, examples in which powder X-ray diffraction (PXRD), Raman spectroscopy and high-precision temperature permitted the monitoring of chemical reactions in real time were presented. The last speaker of the morning session was Dr. Thomas-Xavier Métro (University of Montpelier), who shared with the audience sustainable synthetic strategies to prepare peptides using ball milling and extrusion techniques. Moreover, an unprecedented approach using liquid-assisted grinding (LAG) for the mechanosynthesis of 17O-enriched molecules was described.

The final session of the symposium began with Dr. Franziska Emmerling (Federal Institute for Materials Research and Testing). In her talk entitled “Mechanistic Investigations of Mechanosynthesis”, Dr. Emmerling showed the advantages of merging in-situ XRD with Raman spectroscopy to characterize various polymorphic forms of cocrystals and especially to understand the kinetic and thermodynamic aspects of mechanochemical reactions. Then, Prof. Felipe García (Nanyang Technological University) was in charge of giving the last scientific presentation of this symposium, which covered extensive work on the synthesis of compounds, metal complexes and cocrystals containing main group elements by mechanochemistry.

During the closing remarks, Dr. José G. Hernández underlined the success of the Beilstein Organic Chemistry Symposium based on the quality of the oral and poster presentations, the impeccable organization of the event by Dr. Michael Penk, and especially based on the level of interaction between the participants, which helped strengthening the mechanochemistry community.

Karen Janella Ardila-Fierro and José G. Hernández

Scientific Program

Talks

 

TUESday, 13   NOVEMBER

9:00
Welcome and Introduction

Session chair: James Mack

9:20
Understanding, scaling and commercialising mechanochemical synthesis
Stuart L. James / Queen's University Belfast, UK

10:00
Thermodynamics and stability in mechanochemistry and mechanochemically-made materials
Tomislav Friščić / McGill University, Canada

10:40
Coffee break

11:10
Quantitative studies of polymer mechanochemistry
Stephen Craig / Duke University, USA

11:50
Elucidating covalent mechanochemistry with single-molecule force spectroscopy and quantum chemistry
Martin K. Beyer / University of Innsbruck, Austria

12:30
Lunch

 

Session chair: Stuart L. James

13:50
Episode IX: the ball-mill strikes back
Frédéric Lamaty / University of Montpellier, France

14:30
Nucleic acid mechanochemistry - a 150-year love affair
Joseph S. Vyle / Queen's University Belfast, UK

15:10
Coffee break

15:40
Mechanochemical synthesis of cyclic compounds
Guan-Wu Wang / University of Science and Technology of China, China

16:20
Diversity-oriented synthesis based on a mechanochemical multicomponent reaction
José Carlos Menendez / Complutense University of Madrid, Spain

17:00
End of talks

 

POSTER SESSION - PART 1

17:30
Presentation and discussion of posters

19:30
End of poster session

19:30
Dinner

 

WEDNESDAY, 14 November

Session chair: Tomislav Friščić

9:00
Mechanochemistry in C–H-bond functionalization
Carsten Bolm / RWTH Aachen University, Germany

9:40
Developing selective reactions under mechanochemical onditions
James Mack / University of Cincinnati, USA

10:20
Coffee break

10:50
Computational covalent mechanochemistry: providing molecular insight
Dominik Marx / Ruhr University Bochum, Germany

11:30
Linking mechanochemistry with protein folding with single bond resolution
Sergi Garcia-Manyes / King's College London, UK

12:10
Lunch

 

Session chair: Deborah E. Crawford

13:50
Mech@nochemistry: bridging tradition and innovation in organic synthesis
Evelina Colacino / University of Montpellier & Institute Charles Gerhardt of Montpellier, France

14:30
Mechanochemistry of gaseous reagents
José G. Hernández / RWTH Aachen University, Germany

15:10
Coffee break

15:40
Mechanochemical and mechanocatalytic reactions in ball mills
Olena Vozniuk / Max Planck Institute for Coal Research, Germany

16:20
Mechanochemical pathways towards polymer framework and porous carbon materials
Lars Borchardt / TU Dresden, Germany

17:00
End of talks

 

POSTER SESSION - PART 2

17:30
Presentation and discussion of posters

19:30
End of poster session

19:30
Dinner

 

 

THURSday, 15 November

Session chair: Frédéric Lamaty

9:00
Extrusion: an efficient technique for the manufacture of organic compounds and materials
Deborah E. Crawford / Queen's University Belfast, UK

9:40
Influence of stressing conditions regarding efficiency and energy consumption of Knoevenagel syntheses
Sandra Breitung-Faes / Braunschweig University of Technology, Germany

10:20
Coffee break

10:50
In situ monitoring of mechanochemical reactions for new advances in organic chemistry
Krunoslav Užarević / Ruđer Bošković Institute, Croatia

11:30
From batch to flow in organic mechanosynthesis
Thomas-Xavier Métro / Institut des Biomolécules Max Mousseron, France

12:10
Lunch

 

Session chair: Niamh Willis-Fox

13:30
Mechanistic investigations of mechanosyntheses
Franziska Emmerling / Federal Institute for Materials Research and Testing, Germany

14:10
Mechanochemical synthesis of main group compounds and complexes
Felipe Garcia / Nanyang Technological University, Singapore

14:50
Final words, farewell

15:00
End of program

19:00
Dinner

Posters

Part 1 - Tuesday, 13 November

 

No. 1:
Elucidating the mechanocatalytic conversion of biomass
Saeed Amirjalayer / University of Münster

No. 2:
Discovering chemical reactivity by mechanochemistry: the case of CaC2 in copper-catalyzed A3 couplings
Karen J. Ardila-Fierro / RWTH Aachen University

No. 3:
Tailor-made force-probes for wavelength-orthogonal stress-sensing
Christoph Baumann / DWI - Leibniz Institute for Interactive Materials

No. 4:
A solvent-free approach towards porous polymers – mechanochemical polymerization
Lars Borchardt / TU Dresden

No. 5:
Impact of a mechanical bond on the activation of a mechanophore
Guillaume De Bo / University of Manchester

No. 6:
Mechanochemistry of disulfides – first principles simulations
Przemysław Dopieralski / Ruhr-University Bochum

No. 7:
“One-pot two-step” mechanochemical synthesis of group 13 salen complexes
Felipe García / Nanyang Technological University

No. 8:
Development of cyclophosphazane-based hybrid organic-inorganic multicomponent cocrystals using mechanochemistry
Felipe García / Nanyang Technological University

No. 9:
Nanographenes by solvent-free syntheses – the mechanochemical Scholl reaction
Sven Grätz / TU Dresden

Part 2 - Wednesday, 14 November

 

No. 10:
Mechanochemical polymer synthesis
Jeung Gon Kim / Chonbuk National University

No. 11:
Mechanochemical indicator based on tetraphenylethylene
Martin Krupička / University of Chemistry and Technology, Prague

No. 12:
Cocrystal intermediate in a mechanochemical organic covalent reaction 
Stipe Lukin / Ruđer Bošković Institute

No. 13:
Mechanochemical formation of C–N bonds
William I. Nicholson / Cardiff University

No. 14:
Mechanical activation of a copper biscarbene catalyst using single-molecule force spectroscopy
Matthew S. Sammon / University of Innsbruck

No. 15:
Single-molecule force spectroscopy of polyethylene glycol under variation of solvents and salt concentrations
Simone Schirra / University of Innsbruck

No. 16:
Upgrading dimethylamine borane dehydrocoupling by mechanochemistry
Christian Schumacher / RWTH Aachen University

No. 17:
Polymer mechanochemistry: manufacturing is now a force to be reckoned with
Niamh Willis-Fox / University of Cambridge

No. 18:
Synthesis of potential anti-cancer agents using mechanochemistry
Jordan J. Wilson / Queen’s University Belfast

Symp Mechano