Impact of Positional Isomerism on Pathway Complexity in Aqueous Media.
BODIPY dyes
amphiphilic systems
aqueous self-assembly
cooperativity
pathway complexity
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
27 03 2020
27 03 2020
Historique:
received:
09
09
2019
revised:
30
10
2019
pubmed:
19
12
2019
medline:
19
12
2019
entrez:
19
12
2019
Statut:
ppublish
Résumé
Pathway complexity has become an important topic in recent years due to its relevance in the optimization of molecular assembly processes, which typically require precise sample preparation protocols. Alternatively, competing aggregation pathways can be controlled by molecular design, which primarily rely on geometrical changes of the building blocks. However, understanding how to control pathway complexity by molecular design remains elusive and new approaches are needed. Herein, we exploit positional isomerism as a new molecular design strategy for pathway control in aqueous self-assembly. We compare the self-assembly of two carboxyl-functionalized amphiphilic BODIPY dyes that solely differ in the relative position of functional groups. Placement of the carboxyl group at the 2-position enables efficient pairwise H-bonding interactions into a single thermodynamic species, whereas meso-substitution induces pathway complexity due to competing hydrophobic and hydrogen bonding interactions. Our results show the importance of positional engineering for pathway control in aqueous self-assembly.
Identifiants
pubmed: 31849157
doi: 10.1002/anie.201911531
pmc: PMC7154731
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
5675-5682Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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