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A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores

Liquid chromophores constitute a rare but intriguing class of molecules that are in high demand for the design of luminescent inks, liquid semiconductors, and solar energy storage materials. The most common way to achieve liquid chromophores involves the introduction of long alkyl chains, which, how...

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Autores principales: Kushwaha, Khushbu, Yu, Liyang, Stranius, Kati, Singh, Sandeep Kumar, Hultmark, Sandra, Iqbal, Muhammad Naeem, Eriksson, Lars, Johnston, Eric, Erhart, Paul, Müller, Christian, Börjesson, Karl
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6382313/
https://www.ncbi.nlm.nih.gov/pubmed/30828534
http://dx.doi.org/10.1002/advs.201801650
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author Kushwaha, Khushbu
Yu, Liyang
Stranius, Kati
Singh, Sandeep Kumar
Hultmark, Sandra
Iqbal, Muhammad Naeem
Eriksson, Lars
Johnston, Eric
Erhart, Paul
Müller, Christian
Börjesson, Karl
author_facet Kushwaha, Khushbu
Yu, Liyang
Stranius, Kati
Singh, Sandeep Kumar
Hultmark, Sandra
Iqbal, Muhammad Naeem
Eriksson, Lars
Johnston, Eric
Erhart, Paul
Müller, Christian
Börjesson, Karl
author_sort Kushwaha, Khushbu
collection PubMed
description Liquid chromophores constitute a rare but intriguing class of molecules that are in high demand for the design of luminescent inks, liquid semiconductors, and solar energy storage materials. The most common way to achieve liquid chromophores involves the introduction of long alkyl chains, which, however, significantly reduces the chromophore density. Here, strategy is presented that allows for the preparation of liquid chromophores with a minimal increase in molecular weight, using the important class of perylenes as an example. Two synergistic effects are harnessed: (1) the judicious positioning of short alkyl substituents, and (2) equimolar mixing, which in unison results in a liquid material. A series of 1‐alkyl perylene derivatives is synthesized and it is found that short ethyl or butyl chains reduce the melting temperature from 278 °C to as little as 70 °C. Then, two low‐melting derivatives are mixed, which results in materials that do not crystallize due to the increased configurational entropy of the system. As a result, liquid chromophores with the lowest reported molecular weight increase compared to the neat chromophore are obtained. The mixing strategy is readily applicable to other π‐conjugated systems and, hence, promises to yield a wide range of low molecular weight liquid chromophores.
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spelling pubmed-63823132019-03-01 A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores Kushwaha, Khushbu Yu, Liyang Stranius, Kati Singh, Sandeep Kumar Hultmark, Sandra Iqbal, Muhammad Naeem Eriksson, Lars Johnston, Eric Erhart, Paul Müller, Christian Börjesson, Karl Adv Sci (Weinh) Full Papers Liquid chromophores constitute a rare but intriguing class of molecules that are in high demand for the design of luminescent inks, liquid semiconductors, and solar energy storage materials. The most common way to achieve liquid chromophores involves the introduction of long alkyl chains, which, however, significantly reduces the chromophore density. Here, strategy is presented that allows for the preparation of liquid chromophores with a minimal increase in molecular weight, using the important class of perylenes as an example. Two synergistic effects are harnessed: (1) the judicious positioning of short alkyl substituents, and (2) equimolar mixing, which in unison results in a liquid material. A series of 1‐alkyl perylene derivatives is synthesized and it is found that short ethyl or butyl chains reduce the melting temperature from 278 °C to as little as 70 °C. Then, two low‐melting derivatives are mixed, which results in materials that do not crystallize due to the increased configurational entropy of the system. As a result, liquid chromophores with the lowest reported molecular weight increase compared to the neat chromophore are obtained. The mixing strategy is readily applicable to other π‐conjugated systems and, hence, promises to yield a wide range of low molecular weight liquid chromophores. John Wiley and Sons Inc. 2019-01-15 /pmc/articles/PMC6382313/ /pubmed/30828534 http://dx.doi.org/10.1002/advs.201801650 Text en © 2019 The Authors. Published by WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Kushwaha, Khushbu
Yu, Liyang
Stranius, Kati
Singh, Sandeep Kumar
Hultmark, Sandra
Iqbal, Muhammad Naeem
Eriksson, Lars
Johnston, Eric
Erhart, Paul
Müller, Christian
Börjesson, Karl
A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores
title A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores
title_full A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores
title_fullStr A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores
title_full_unstemmed A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores
title_short A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores
title_sort record chromophore density in high‐entropy liquids of two low‐melting perylenes: a new strategy for liquid chromophores
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6382313/
https://www.ncbi.nlm.nih.gov/pubmed/30828534
http://dx.doi.org/10.1002/advs.201801650
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