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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(01): 041-046
DOI: 10.1055/s-0040-1705124
Focus Issue: Structure to Function in Supramolecular Polymers and Materials
Short Communication
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2020) The Author(s).

Unconventional Chiral Amplification in Luminescent Supramolecular Polymers Based on Trisbiphenylamine-tricarboxamides

Yeray Dorca 
a   Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, s/n, 28040, Madrid, Spain
,
Cristina Naranjo 
a   Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, s/n, 28040, Madrid, Spain
,
Goutam Ghosh 
b   Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
,
Rafael Gómez 
a   Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, s/n, 28040, Madrid, Spain
,
Gustavo Fernández 
b   Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
,
Luis Sánchez 
a   Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, s/n, 28040, Madrid, Spain
› Author Affiliations Funding Information Financial support by the MINECO of Spain (CTQ2017-82706-P) and Comunidad de Madrid (P2018/NMT-4389) is acknowledged.
Further Information

Publication History

Received: 17 December 2019

Accepted after revision: 29 January 2020

Publication Date:
30 March 2020 (online)

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Abstract

We describe the synthesis of two propeller-shaped, emissive trisbiphenylamines 1 and (S)-2. Whilst achiral 1 forms supramolecular polymers following a cooperative mechanism, the self-assembly of chiral (S)-2 can be described by an isodesmic mechanism. Despite the isodesmic character of the supramolecular polymerization of (S)-2, an efficient transfer of chirality from the embedded point chirality of the peripheral side chains to the aggregates is demonstrated. The co-assembly of 1 and (S)-2 in a sergeants-and-soldiers experiment shows a very different dichroic response to that registered for pristine (S)-2, with a copolymerization curve displaying two transitions. Both these transitions coincide with those observed for the pristine achiral and chiral components, thus suggesting a self-sorting effect.

Key words

Cooperativity - isodesmic - helical structures - supramolecular polymerization - triarylamines

Supporting Information

Supporting information for this article is available online at https://doi.org.


Supporting Information

 

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