• Home
  1. Home
  2. Complex surface architectures: the discovery of the third orthogonal dynamic covalent bond
Doctoral thesis
OA Policy
English

Complex surface architectures: the discovery of the third orthogonal dynamic covalent bond

Contributors

Lascano, Santiago

Directors

Matile, Stefan

Defense date

2016-12-21

Abstract

The SOSIP-TSE methodology was until recently based on only two orthogonal dynamic covalent bonds : Disulfides and hydrazones. The introduction of boronate esters to these architectures was possible, but they lacked orthogonality. We here show the first known example of three completely orthogonal dynamic covalent bonds, namely disulfides, hydrazones and boronate esters. After chosing the appropriate substrates, with adapted reactivity and stability, the conditions for the orthogonal exchange reactions were determined by experiments in solution. The compatibility of this system with surface architectures was then determined by 1H-NMR and mass spectrometry. The system was further enhanced by using more stable boronate esters, that showed impressive stability in acidic and aqueous conditions, while keeping their dynamic character when needed. These new more stable boronate esters were also shown to have impressive characteristics in surface architectures, showing their potential.

Keywords

  • Orthogonal dynamic covalent bond
  • Orthogonality
  • Dynamic covalent bond
  • Boronate ester
  • Boronic ester
  • Disulfide
  • Hydrazone
  • Surface architecture
  • SOSIP
  • Supramolecular architecture
  • Artificial photosystem

UNIGE affiliation entities

UNIGE research groups

Citation (ISO format)

LASCANO, Santiago. Complex surface architectures: the discovery of the third orthogonal dynamic covalent bond. Doctoral Thesis, 2016. doi: 10.13097/archive-ouverte/unige:91997

Main files (1)

Thesis

Identifiers

1098views
625downloads

Technical informations

Creation

15/02/2017 12:13:00

First validation

15/02/2017 12:13:00

Update

13/10/2025 20:13:18

Status update

15/03/2023 01:23:32

Last indexation

02/11/2025 20:18:39
All rights reserved by Archive ouverte UNIGE and the University of Geneva
OpenAIRE Indexed & Validated