ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2019
A Record Chromophore Density in High-Entropy Liquids of Two Low-Melting Perylenes: A New Strategy for Liquid Chromophores.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed, 19 citations in OpenAlex.
- Harnessing inhomogeneous π-aggregates: a new path to optical modulation in methyl salicylate-based solvent-free liquids.Chemical science · 2025Article
- Interplay between Polaritonic and Molecular Trap States.The journal of physical chemistry. C, Nanomaterials and interfaces · 2022Article
- Exciton Delocalization Counteracts the Energy Gap: A New Pathway toward NIR-Emissive Dyes.Journal of the American Chemical Society · 2021Article
- Room-temperature phosphorescence of a supercooled liquid: kinetic stabilisation by desymmetrisation.Chemical science · 2021Article
- Fluorescent Liquid Tetrazines.Molecules (Basel, Switzerland) · 2021Article
- Vitrification of octonary perylene mixtures with ultralow fragility.Science advances · 2021Article
- Entropic Mixing Allows Monomeric-Like Absorption in Neat BODIPY Films.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- A Record Chromophore Density in High-Entropy Liquids of Two Low-Melting Perylenes: A New Strategy for Liquid Chromophores.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2019Article
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Authors and funding
11 authors at 4 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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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