Carbodiimide-driven dimerization and self-assembly of artificial, ribose-based amphiphiles

OPen Access Repositorium der Universität Ulm (OPARU) (Ulm University)

Abstract

The aqueous self-assembly of amphiphiles into aggregates such as micelles and vesicles has been widely investigated over the past decades with applications ranging from materials science to drug delivery. The combination of characteristic properties of nucleic acids and amphiphiles is of substantial interest to mimic biological self-organization and compartmentalization. Herein, we present ribose- and ribonucleotide-based amphiphiles and investigate their self-assembly as well as their fundamental reactivity. We found that various types of aggregates are formed, ranging in size from nanometers to micrometers and all amphiphiles exhibit aggregation-induced emission (AIE) in solution as well as in the solid state. We also observed that the addition of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) leads to rapid and selective dimerization of the amphiphiles into pyrophosphates, which decreases the critical aggregation concentration (CAC) by a factor of 25 when compared to the monomers. Since the propensity for amphiphile dimerization is correlated with their tendency to self-assemble, our results may be relevant for the formation of rudimentary compartments under prebiotic conditions.

Authors 7

1. Jing Sun

   Universität Ulm

   Affiliation as printed

   Institute of Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

   These authors contributed equally to this work

2. Julian Vogel

   Universität Ulm

   Affiliation as printed

   Institute of Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

   These authors contributed equally to this work

3. Lisa Chen

   Universität Ulm

   Affiliation as printed

   Institute of Macromolecular and Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

4. A. Lennart Schleper

   Universität Ulm

   Affiliation as printed

   Institute of Macromolecular and Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

5. Tim Bergner

   Universität Ulm

   Affiliation as printed

   Central Facility for Electron Microscopy, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

6. Alexander J. C. Kuehne Aachen

   Universität Ulm · DWI – Leibniz Institute for Interactive Materials

   Affiliation as printed

   DWI – Leibniz-Institute for Interactive Materials Forckenbeckstraße 50 52074 Aachen Germany

   Institute of Macromolecular and Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

7. Max von Delius corresponding

   Universität Ulm

   Affiliation as printed

   Institute of Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany