A Record Chromophore Density in High-Entropy Liquids of Two Low-Melting Perylenes: A New Strategy for Liquid Chromophores
Journal article, 2019

Weinheim 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.

low melting solids

alkylation

high quantum yield

liquid fluorophores

thermodynamic mixing

Author

Khushbu Kushwaha

University of Gothenburg

Liyang Yu

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Christian Müller Group

Kati Stranius

University of Gothenburg

Sandeep Kumar Singh

Chalmers, Physics, Materials and Surface Theory

Sandra Hultmark

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Christian Müller Group

Muhammad Naeem Iqbal

Stockholm University

Lars Eriksson

Stockholm University

Eric Johnston

Sigrid Therapeutics AB

Paul Erhart

Chalmers, Physics, Materials and Surface Theory

Christian Müller

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Christian Müller Group

Karl Börjesson

University of Gothenburg

Advanced Science

2198-3844 (ISSN)

Vol. 6 4 1801650

Subject Categories

Polymer Chemistry

Polymer Technologies

Other Chemistry Topics

DOI

10.1002/advs.201801650

More information

Latest update

3/8/2019 3