Issue 4, 2021

Exploring the tubular self-assembly landscape of dinucleobase amphiphiles in water

Abstract

The design and production of the next generations of synthetic aqueous self-assembled systems able to mimic some biological features will require increasingly sophisticated monomer constituents that make use of additional interactions to hydrophibic effects to attain enhanced structural and functional complexity. Here, we broadly investigate the aqueous self-assembly of dinucleobase amphiphilic monomers into helical nanotubes under a wide range of different conditions of temperature, concentration, solvent composition and pH. Such monomers comprise an amphiphilic π-conjugated central block, endowed with a lipophilic chiral tail and a hydrophilic group that can be made anionic (carboxylate), neutral (glycol) or cationic (ammonium), disubstituted with complementary guanine and cytosine nucleobases at each termini. These molecules self-assemble into amphiphilic nanotubes in water but, when subjected to diverse (drastic) changes in the experimental conditions, undergo either disassembly into monomers, chiral reorganization, or a morphological restructuration into globular objects due to dehydration of the peripheral hydrophilic groups.

Graphical abstract: Exploring the tubular self-assembly landscape of dinucleobase amphiphiles in water

Supplementary files

Article information

Article type
Research Article
Submitted
28 محرم 1442
Accepted
18 ربيع الثاني 1442
First published
23 ربيع الثاني 1442

Org. Chem. Front., 2021,8, 686-696

Exploring the tubular self-assembly landscape of dinucleobase amphiphiles in water

P. B. Chamorro, F. Aparicio, R. Chamorro, N. Bilbao, S. Casado and D. González-Rodríguez, Org. Chem. Front., 2021, 8, 686 DOI: 10.1039/D0QO01110J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements