Project

Back to overview

Synthetic Biosupramolecular Systems at Work

English title Synthetic Biosupramolecular Systems at Work
Applicant Matile Stefan
Number 162363
Funding scheme Project funding
Research institution Département de Chimie Organique Université de Genève
Institution of higher education University of Geneva - GE
Main discipline Organic Chemistry
Start/End 01.10.2015 - 30.09.2017
Approved amount 841'554.00
Show all

Keywords (15)

Multicomponent surface architectures; Catalysis; Supramolecular functional systems; Dynamic covalent bonds; Enamine chemistry; Fluorescent membrane probes; Anion-pi interactions; Artificial photosystems; Mechanosensitive bonds; Ionpair-p interactions; Multistep organic synthesis; Enolate chemistry; Cellular uptake; Self-sorting; Spectral tuning

Lay Summary (French)

Lead
L’objectif général de ce projet est de créer des systèmes moléculaires et supramoléculaires avec des activités importants. Le premier sujet spécifique concerne des catalyseurs qui réalisent des transformations moléculaires sur des surfaces aromatiques avec des interactions inédites en chimie organique. Dans la quête de nouveaux matériaux, le développement de méthodes pour construire des architectures moléculaires d’une complexité croissante sur des surfaces solides apporte une contribution importante. Enfin, les efforts dirigés vers la découverte de stratégies nouvelles pour pénétrer dans la cellule et « visualiser l’invisible » dans la membrane cellulaire sont particulièrement intéressants du point de vue de la biologie et la médecine.
Lay summary

La chimie, et la chimie organique en particulier, permet de créer de la matière nouvelle. L’importance sociétale de cette expertise unique, permettant de préparer presque n’importe quelle petite molécule, est avérée (>25% des exportations en Suisse, etc.). En revanche, la création de systèmes moléculaires et supramoléculaires accomplissant des fonctions importantes reste très difficile. Les quatre sous-projets de ce projet abordent ce défi par différents angles. Avec des interactions innovantes, des liaisons dynamiques ou mécanosensibles mais surtout des interactions anion-π, nous chercherons de nouveaux outils pour la construction de ces systèmes fonctionnels. Cet objectif est comparable à l’introduction d’une nouvelle couleur sur la palette d’un peintre. La catalyse « anion-π » sur une surface aromatique, totalement inédite, est un des objectifs principaux. Avec des transformations dynamiques sur la surface cellulaire nous cherchons de nouvelles routes pour apporter des médicaments à l’intérieur des cellules. Des liaisons dynamiques sont aussi prévues pour construire des matériaux fonctionnels de plus en plus sophistiqués directement sur des surfaces solides. Des liaisons mécanosensibles sont utilisées pour visualiser des processus cellulaires autrement invisibles (tension, potentiel membranaire). Bien que fondamentaux par nature, ces projets contribueront sur le long terme à des innovations importantes pour la santé publique (livraison des médicaments, senseurs diagnostiques), l’énergie (optoélectroniques) et l’environnement (meilleurs catalyseurs).

 

Direct link to Lay Summary Last update: 26.09.2015

Responsible applicant and co-applicants

Employees

Publications

Publication
Anion–π Catalysis of Diels–Alder Reactions
Liu Le, Cotelle Yoann, Bornhof Anna Bea, Besnard Céline, Sakai Naomi, Matile Stefan (2017), Anion–π Catalysis of Diels–Alder Reactions, in Angewandte Chemie - International Edition, (42), 13066-13069.
Anion-π transaminase mimics
Liu Le, Matile Stefan (2017), Anion-π transaminase mimics, in Supramolecular Chemistry, (10), 702-706.
Anion-π Catalysis on Fullerenes
López-Andarias Javier, Frontera Antonio, Matile Stefan (2017), Anion-π Catalysis on Fullerenes, in Journal of the American Chemical Society, (38), 13296-13299.
Anion-π Catalysts with Axial Chirality
Wang Chao, Matile Stefan (2017), Anion-π Catalysts with Axial Chirality, in Chemistry - A European Journal, (49), 11955-11960.
Efficient Delivery of Quantum Dots into the Cytosol of Cells Using Cell-Penetrating Poly(disulfide)s
Derivery Emmanuel, Bartolami Eline, Matile Stefan, Gonzalez-Gaitan Marcos (2017), Efficient Delivery of Quantum Dots into the Cytosol of Cells Using Cell-Penetrating Poly(disulfide)s, in Journal of the American Chemical Society, (30), 10172-10175.
Planarizable Push–Pull Probes: Overtwisted Flipper Mechanophores
Macchione Mariano, Chuard Nicolas, Sakai Naomi, Matile Stefan (2017), Planarizable Push–Pull Probes: Overtwisted Flipper Mechanophores, in ChemPlusChem, (7), 1062-1066.
Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface
Neuhaus Frederik, Zobi Fabio, Brezesinski Gerald, Dal Molin Marta, Matile Stefan, Zumbuehl Andreas (2017), Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface, in Beilstein Journal of Organic Chemistry, 13, 1099-1105.
Epidithiodiketopiperazines: Strain-Promoted Thiol-Mediated Cellular Uptake at the Highest Tension
Zong Lili, Bartolami Eline, Abegg Daniel, Adibekian Alexander, Sakai Naomi, Matile Stefan (2017), Epidithiodiketopiperazines: Strain-Promoted Thiol-Mediated Cellular Uptake at the Highest Tension, in ACS Central Science, (5), 449-453.
Electric-Field-Assisted Anion-π Catalysis
Akamatsu Masaaki, Sakai Naomi, Matile Stefan (2017), Electric-Field-Assisted Anion-π Catalysis, in Journal of the American Chemical Society, (19), 6558-6561.
Strain-Promoted Thiol-Mediated Cellular Uptake of Giant Substrates: Liposomes and Polymersomes
Chuard Nicolas, Gasparini Giulio, Moreau Dimitri, Lörcher Samuel, Palivan Cornelia, Meier Wolfgang, Sakai Naomi, Matile Stefan (2017), Strain-Promoted Thiol-Mediated Cellular Uptake of Giant Substrates: Liposomes and Polymersomes, in Angewandte Chemie - International Edition, (11), 2947-2950.
Strained cyclic disulfides enable cellular uptake by reacting with the transferrin receptor
Abegg Daniel, Gasparini Giulio, Hoch Dominic G., Shuster Anton, Bartolami Eline, Matile Stefan, Adibekian Alexander (2017), Strained cyclic disulfides enable cellular uptake by reacting with the transferrin receptor, in Journal of the American Chemical Society, (1), 231-238.
Anion-π catalysis: Bicyclic products with four contiguous stereogenic centers from otherwise elusive diastereospecific domino reactions on π-acidic surfaces
Liu Le, Cotelle Yoann, Klehr Juliane, Sakai Naomi, Ward Thomas R., Matile Stefan (2016), Anion-π catalysis: Bicyclic products with four contiguous stereogenic centers from otherwise elusive diastereospecific domino reactions on π-acidic surfaces, in Chemical Science, (5), 3770-3774.
Catalysis with Chalcogen Bonds
Benz Sebastian, López-Andarias Javier, Mareda Jiri, Sakai Naomi, Matile Stefan (2016), Catalysis with Chalcogen Bonds, in Angewandte Chemie - International Edition, (3), 812-815.
Sidechain Engineering in Cell-Penetrating Poly(disulfide)s
Morelli Paola, Matile Stefan (2016), Sidechain Engineering in Cell-Penetrating Poly(disulfide)s, in Helvetica Chimica Acta, (3), e1600370 -e1600370.
Twisted Push-Pull Probes with Turn-On Sulfide Donors
Verolet Quentin, Dal Molin Marta, Colom Adai, Roux Aurélien, Guénée Laure, Sakai Naomi, Matile Stefan (2016), Twisted Push-Pull Probes with Turn-On Sulfide Donors, in Helvetica Chimica Acta, (2), e1600328-e1600328.
Activation of Cell-Penetrating Peptides with Ionpair-π Interactions and Fluorophiles
Chuard Nicolas, Fujisawa Kaori, Morelli Paola, Saarbach Jacques, Winssinger Nicolas, Metrangolo Pierangelo, Resnati Giuseppe, Sakai Naomi, Matile Stefan (2016), Activation of Cell-Penetrating Peptides with Ionpair-π Interactions and Fluorophiles, in Journal of the American Chemical Society, (35), 11264-11271.
Anion Transport with Chalcogen Bonds
Benz Sebastian, Macchione Mariano, Verolet Quentin, Mareda Jiri, Sakai Naomi, Matile Stefan (2016), Anion Transport with Chalcogen Bonds, in Journal of the American Chemical Society, (29), 9093-9096.
Asymmetric Anion−π Catalysis of Iminium/Nitroaldol Cascades To Form Cyclohexane Rings with Five Stereogenic Centers Directly on π-Acidic Surfaces
Liu Le, Cotelle Yoann, Avestro Alyssa-Jennifer, Sakai Naomi, Matile Stefan (2016), Asymmetric Anion−π Catalysis of Iminium/Nitroaldol Cascades To Form Cyclohexane Rings with Five Stereogenic Centers Directly on π-Acidic Surfaces, in Journal of the American Chemical Society, (25), 7876-7879.
Surveying the Delivery Methods of CRISPR/Cas9 for ex vivo Mammalian Cell Engineering
Kelton William J., Pesch Theresa, Matile Stefan, Reddy Sai T. (2016), Surveying the Delivery Methods of CRISPR/Cas9 for ex vivo Mammalian Cell Engineering, in CHIMIA International Journal for Chemistry, 70(6), 439-442.
Anion-π enzymes
Cotelle Yoann, Lebrun Vincent, Sakai Naomi, Ward Thomas R., Matile Stefan (2016), Anion-π enzymes, in ACS Central Science, (6), 388-393.
Core-Substituted Naphthalenediimides: LUMO Levels Revisited, in Comparison with Preylenediimides with Sulfur Redox Switches in the Core
Miros François N., Matile Stefan (2016), Core-Substituted Naphthalenediimides: LUMO Levels Revisited, in Comparison with Preylenediimides with Sulfur Redox Switches in the Core, in ChemistryOpen, (3), 219-226.
Interfacing functional systems
Cotelle Yoann, Chuard Nicolas, Lascano Santiago, Lebrun Vincent, Wehlauch Robin, Bohni Nadine, Lörcher Samuel, Postupalenko Viktoriia, Reddy Sai T., Meier Wolfgang, Palivan Cornelia G., Gademann Karl, Ward Thomas R., Matile Stefan (2016), Interfacing functional systems, in Chimia, (6), 418-423.
Ethynyl benziodoxolones: Functional terminators for cell-penetrating poly(disulfide)s
Morelli Paola, Martin-Benlloch Xavier, Tessier Romain, Waser Jerome, Sakai Naomi, Matile Stefan (2016), Ethynyl benziodoxolones: Functional terminators for cell-penetrating poly(disulfide)s, in Polymer Chemistry, (20), 3465-3470.
Unorthodox Interactions at Work
Zhao Yingjie, Cotelle Yoann, Sakai Naomi, Matile Stefan (2016), Unorthodox Interactions at Work, in Journal of the American Chemical Society, (13), 4270-4277.
Anion-π Catalysis of Enolate Chemistry: Rigidified Leonard Turns as a General Motif to Run Reactions on Aromatic Surfaces
Cotelle Yoann, Benz Sebastian, Avestro Alyssa Jennifer, Ward Thomas R., Sakai Naomi, Matile Stefan (2016), Anion-π Catalysis of Enolate Chemistry: Rigidified Leonard Turns as a General Motif to Run Reactions on Aromatic Surfaces, in Angewandte Chemie - International Edition, (13), 4275-4279.
Expanded Chiral Surfaces for Asymmetric Anion-π Catalysis
Akamatsu Masaaki, Matile Stefan (2016), Expanded Chiral Surfaces for Asymmetric Anion-π Catalysis, in Synlett, (7), 1041-1046.
Enolate Stabilization by Anion-π Interactions: Deuterium Exchange in Malonate Dilactones on π-Acidic Surfaces
Miros François N., Zhao Yingjie, Sargsyan Gevorg, Pupier Marion, Besnard Céline, Beuchat César, Mareda Jiri, Sakai Naomi, Matile Stefan (2016), Enolate Stabilization by Anion-π Interactions: Deuterium Exchange in Malonate Dilactones on π-Acidic Surfaces, in Chemistry - A European Journal, (8), 2648-2657.
Asymmetric Anion–π Catalysis on Perylenediimides
Wang Chao, Miros François N., Mareda Jiri, Sakai Naomi, Matile Stefan (2015), Asymmetric Anion–π Catalysis on Perylenediimides, in Angewandte Chemie - International Edition, (46), 14422-14426.
Dipolar Photosystems: Engineering Oriented Push–Pull Components into Double- and Triple-Channel Surface Architectures
Bolag Altan, Sakai Naomi, Matile Stefan (2015), Dipolar Photosystems: Engineering Oriented Push–Pull Components into Double- and Triple-Channel Surface Architectures, in Chemistry - A European Journal, (26), 9006-9014.
Headgroup engineering in mechanosensitive membrane probes
Soleimanpour Saeideh, Colom Adai, Derivery Emmanuel, Gonzalez-Gaitan Marcos, Roux Aurelien, Sakai Naomi, Matile Stefan (2015), Headgroup engineering in mechanosensitive membrane probes, in Chemical Communications, (100), 14450-14453.
The third orthogonal dynamic covalent bond
Lascano Santiago, Zhang Kang Da, Wehlauch Robin, Gademann Karl, Sakai Naomi, Matile Stefan (2015), The third orthogonal dynamic covalent bond, in Chemical Science, (7), 4720-4724.
Turn-On Sulfide π Donors: An Ultrafast Push for Twisted Mechanophores
Verolet Quentin, Rosspeintner Arnulf, Soleimanpour Saeideh, Sakai Naomi, Vauthey Eric, Matile Stefan (2015), Turn-On Sulfide π Donors: An Ultrafast Push for Twisted Mechanophores, in Journal of the American Chemical Society, (50), 15644-15647.
Protein delivery with cell-penetrating poly(disulfide)s
Gasparini Giulio, Matile Stefan (2015), Protein delivery with cell-penetrating poly(disulfide)s, in Chemical Communications, 51(96), 17160-17162.

Collaboration

Group / person Country
Types of collaboration
Sai Reddy Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Marcos Gonzalez-Gaitan Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Karl Gademann Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Aurelien Roux Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
- Research Infrastructure
- Exchange of personnel
Nicolas Winssinger Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Antonio Frontera Spain (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Jiri Mareda Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Pierangelo Matrangolo Italy (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Tom Ward Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
- Exchange of personnel
Andreas Zumbuehl Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Jerome Waser Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Cornelia Palivan Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Eric Vauthey Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication
Alex Adibekian Switzerland (Europe)
- in-depth/constructive exchanges on approaches, methods or results
- Publication

Scientific events

Active participation

Title Type of contribution Title of article or contribution Date Place Persons involved
ICMSE, International Conference Molecular Systems Engineering Talk given at a conference Functional Supramolecular Chemistry 26.08.2017 Basel, Switzerland Bornhof Anna-Bea;
ICMSE, International Conference Molecular Systems Engineering Poster Functional Supramolecular Chemistry 26.08.2017 Basel, Switzerland Benz Sebastian;
Swiss Chemical Society Fall Meeting Poster Functional Supramolecular Chemistry 21.08.2017 Bern, Switzerland Macchione Mariano;
Swiss Chemical Society Fall Meeting Poster Functional Supramolecular Chemistry 21.08.2017 Bern, Switzerland Morelli Paola;
Swiss Chemical Society Fall Meeting Talk given at a conference Functional Supramolecular Chemistry 21.08.2017 Bern, Switzerland Benz Sebastian;
XXV National Meeting of Portuguese Chemical Society (XXVEN-SPQ), Talk given at a conference Functional Supramolecular Chemistry 16.07.2017 Lisbon, Portugal Matile Stefan;
The 29th International Symposium on Chirality (Chirality 2017; ISCD-29) Talk given at a conference Anion-π Catalysis 09.07.2017 Waseda University International Conference Center, Tokyo, Japan Matile Stefan;
ISOCS-27, the 27th International Symposium on Organic Chemistry of Sulfur Talk given at a conference Functional Supramolecular Chemistry 02.07.2017 Jena, Germany Benz Sebastian;
ISMSC-12, the 12th International Symposium on Macrocyclic and Supramolecular Chemistry Poster Functional Supramolecular Chemistry 02.07.2017 Cambridge, Great Britain and Northern Ireland Wang Chao;
ESOC-20, the 20th European Symposium of Organic Chemistry Talk given at a conference Conceptually Innovative Functional Systems 02.07.2017 Cologne, Germany Matile Stefan;
ISMSC-12, the 12th International Symposium on Macrocyclic and Supramolecular Chemistry Poster Functional Supramolecular Chemistry 02.07.2017 Cambridge, Great Britain and Northern Ireland Macchione Mariano;
ISMSC-12, the 12th International Symposium on Macrocyclic and Supramolecular Chemistry Poster Functional Supramolecular Chemistry 02.07.2017 Cambridge, Great Britain and Northern Ireland Zong Lili;
Sorbonne, UPMC Individual talk Conceptually Innovative Ways to Enter into Cells 02.06.2017 Paris, France Matile Stefan;
Gordon Research Conference on “Self-Assembly & Supramolecular Chemistry” Talk given at a conference Conceptually Innovative Supramolecular Functional Systems 21.05.2017 Les Diablerets, Switzerland Matile Stefan;
Chemical Society of Heidelberg Individual talk Functional Supramolecular Chemistry 16.05.2017 Heidelberg, Germany Matile Stefan;
University of Zurich, Seminar Individual talk Conceptually Innovative Functional Systems 29.11.2016 Zurich, Switzerland Matile Stefan;
University of Cambridge Individual talk Unorthodox Interactions at Work 24.11.2016 Cambridge, Great Britain and Northern Ireland Matile Stefan;
Trends in Organic Chemistry Talk given at a conference Supramolecular Systems at Work 23.10.2016 Lund, Sweden Matile Stefan;
Swiss Chemical Society Fall Meeting Poster Functional Supramolecular Chemistry 15.09.2016 Zurich, Switzerland Benz Sebastian;
Swiss Chemical Society Fall Meeting Poster Functional Supramolecular Chemistry 15.09.2016 Zurich, Switzerland Morelli Paola;
ISOCS-27, the 27th International Symposium on Organic Chemistry of Sulfur Talk given at a conference Supramolecular Systems at Work 24.07.2016 Jena, Germany Matile Stefan;
ISMSC-11, the 11th International Symposium on Macrocyclic and Supramolecular Chemistry Poster Functional Supramolecular Chemistry 10.07.2016 Seoul, Korean Republic (South Korea) Morelli Paola;
ISMSC-11, the 11th International Symposium on Macrocyclic and Supramolecular Chemistry Talk given at a conference Supramolecular Systems at Work 10.07.2016 Seoul, Korean Republic (South Korea) Matile Stefan;
University of Santiago de Compostela Individual talk “Supramolecular Systems at Work, Part 2: Cellular Uptake and Sensing” 29.03.2016 Santiago de Compostela, Spain Matile Stefan;
University of Santiago de Compostela Individual talk Supramolecular Systems at Work, Part 1: Unorthodox Interactions, from Transport to Catalysis 28.03.2016 Santiago de Compostela, Spain Matile Stefan;
Workshop on Supramolecular Systems Chemistry Talk given at a conference Supramolecular Systems at Work 29.02.2016 Barcelona, Spain Matile Stefan;
TU Darmstadt Individual talk Conceptually Innovative Ways to Enter into Cells 11.02.2016 Darmstadt, Germany Matile Stefan;
Tarrant Distinguished Visiting Professor Individual talk Supramolecular Systems at Work, Part 3: Multicomponent Photosystems and Mechanophores 02.12.2015 Gainesville, Florida, United States of America Matile Stefan;
Tarrant Distinguished Visiting Professor Individual talk Supramolecular Systems at Work, Part 2: Cellular Uptake and Sensing 01.12.2015 Gainesville, Florida, United States of America Matile Stefan;
Tarrant Distinguished Visiting Professor Individual talk Supramolecular Systems at Work, Part 1: Exotic Interactions, from Transport to Catalysis 30.11.2015 Gainesville, Florida, United States of America Matile Stefan;
ISACS-18, the 18th International Symposium on Advancing the Chemical Sciences Talk given at a conference Supramolecular Systems at Work 15.11.2015 Bangalore, India Matile Stefan;


Communication with the public

Communication Title Media Place Year
Media relations: print media, online media Please see list of publication Western Switzerland International German-speaking Switzerland 2016

Associated projects

Number Title Start Funding scheme
141825 NCCR MSE: Molecular Systems Engineering (phase I) 01.07.2014 National Centres of Competence in Research (NCCRs)
128746 A CryoProbe for the Chemistry Section of the University of Geneva 01.12.2009 R'EQUIP
144953 Open access MALDI for the chemistry, biochemistry and pharmaceutical sciences sections of the University of Geneva 01.09.2013 R'EQUIP
150000 Synthetic Biosupramolecular Systems at Work 01.10.2013 Project funding
113020 Acquisition af a Circular Dichroism Spectrometer 01.11.2006 R'EQUIP
67459 R'EQUIP 2002: Installation of a Modern Light Scattering Facility 01.07.2002 R'EQUIP
125781 NCCR Chemical Biology: Visualisation and Control of Biological Processes Using Chemistry (phase I) 01.12.2010 National Centres of Competence in Research (NCCRs)
175486 Synthetic Biosupramolecular Systems at Work 01.10.2017 Project funding
170744 NanoUHPLC-ESI-HRMS/MS platform with Ion Mobility Spectrometry for the Sections of Chemistry, Biochemistry, Biology and Pharmaceutical Sciences of the University of Geneva 01.01.2017 R'EQUIP

Abstract

The general objective of this proposal is to develop conceptually innovative approaches to functional biosupramolecular systems for use in materials sciences, chemical sciences and life sciences. Particular emphasis is on lessons from nature and the integration of unorthodox interactions. The specific aims are(a) to contribute to discovery and development of catalysis with anion-p interactions and ionpair-p interactions as such (focus on covalent approaches, trifunctional catalysis), (b) to contribute to the development of synthetic methods to build functional surface architectures of highest possible structural sophistication (focus on self-sorting with unorthodox interactions, push-pull stacks, donor-acceptor stacks), and(c) to contribute to the development of thiol-mediated uptake as new pathway to enter into cells (focus on cell-penetrating poly(disulfide)s, ring tension) and to discovery and development of mechanosensitive fluorescent probes (focus on heteroatom-bridged, core-expanded oligothiophene "flippers" in membranes).Specific aim a contributes to ongoing efforts to expand the interactions available to create function, a fundamental effort comparable to adding more colors to the painter’s palette. The likely identification truly fundamental principles in catalysis that do not yet exist in the literature at all is very special and very exciting, calls for highest attention and promises much impact in the chemical sciences. In this grant period, we aim to explore covalent approaches to secure safe insights on these "hot" topics with highest possible accuracy, to discover new catalyst design principles for enolate and enamine chemistry with anion-p interactions (trifunctional systems, Leonard turns, assistance from halogen bonds), and to move, step-by-step, from covalent to non-covalent systems with ionpair-p interactions, with particular emphasis on spectral tuning, excited-state interactions and frustrated ion pairs.Specific aim b focuses on the development of synthetic methods to build multicomponent surface architectures of highest possible sophistication with highest possible precision. This is of interest because biological function is achieved by most complex (and most beautiful) molecular architectures, and synthetic methods to build similarly refined organic materials are underdeveloped. In this grant period, we aim to couple templated self-sorting (TSS) and templated stack exchange (TSE) in multicomponent surface architectures made by the so-called SOSIP-TSE method (developed in this group, based on orthogonal dynamic covalent chemistry). This unprecedented synthetic approach is expected to provide access to the next level of sophistication, and thus to topics that are important in the materials sciences but otherwise difficult to address.Specific aim c elaborates on the usefulness of synthetic organic chemistry to address two important challenges in the life sciences. Dynamic covalent disulfide-exchange chemistry on cell surfaces is proposed to be most powerful with cell-penetrating poly(disulfide)s that are covalently recharged with ring tension, and mechanosensitive fluorescent "flippers" with heteroatom bridges and core-expanded surfaces are proposed to be best to image characteristics of biomembranes, including the hard-to-measure but biologically important tension.All projects are based on target-oriented multistep organic synthesis and live from intertopical crossfertilization. This strategy provides the educational environment that can form ambitious, broad-minded scientists (50% of former group members work in academia). With regard to significance, productivity and probability of success, research from this group has appeared regularly in the top journals (40 JACS, 3 Science, etc), in plenary lectures, and in the media. Continuation on this level is expected.
-