Cargando…
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...
Autores principales: | , , , , , , , , , , |
---|---|
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 |
_version_ | 1783396649432776704 |
---|---|
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. |
format | Online Article Text |
id | pubmed-6382313 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT kushwahakhushbu arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT yuliyang arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT straniuskati arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT singhsandeepkumar arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT hultmarksandra arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT iqbalmuhammadnaeem arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT erikssonlars arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT johnstoneric arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT erhartpaul arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT mullerchristian arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT borjessonkarl arecordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT kushwahakhushbu recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT yuliyang recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT straniuskati recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT singhsandeepkumar recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT hultmarksandra recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT iqbalmuhammadnaeem recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT erikssonlars recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT johnstoneric recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT erhartpaul recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT mullerchristian recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores AT borjessonkarl recordchromophoredensityinhighentropyliquidsoftwolowmeltingperylenesanewstrategyforliquidchromophores |