Unveiling the Role of Hydrogen Bonds in Luminescent N‐Annulated Perylene Liquid Crystals
| Autor: | Elisa E. Greciano, Luis Sánchez, Bartolome Soberats, Manuel A. Martínez, Sergi Bujosa |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Full Paper
Chemistry Hydrogen bond Discotic liquid crystal Organic Chemistry Hexagonal phase General Chemistry self-assembly Full Papers Catalysis functional materials discotic liquid crystals chemistry.chemical_compound Crystallography Liquid crystal Amide hydrogen bonds Structural isomer Molecule Perylene N-annulated perylenes |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | We report the liquid‐crystalline (LC) and luminescent properties of a series of N‐annulated perylenes (1–4) in whose molecular structures amide and ester groups alternate. We found that the LC properties of these compounds not only depend on the number of hydrogen‐bonding units, but also on the relative position of the amide linkers in the molecule. The absence of amide groups in compound 1 leads to no LC properties, whereas four amide groups induce the formation of a wide temperature range columnar hexagonal phase in compound 4. Remarkably, compound 3, with two amide groups in the inner part of the structure, stabilizes the columnar LC phases better than its structural isomer 2, with the amide groups in the outer part of the molecule. Similarly, we found that only compounds 1 and 2, which have no hydrogen bonding units in the inner part of the molecule, exhibit luminescence vapochromism upon exposure to organic solvent vapors. Getting into position: The position of hydrogen‐bonding amide groups affects the properties of a series of luminescent N‐annulated perylenes that self‐assemble into nanostructured liquid‐crystalline columnar phases. The liquid crystals with the amide linkers close to the central perylene core exhibit liquid‐crystalline phases with a wider temperature range. In contrast, perylenes with ester groups, instead of amides, close to the central core exhibit vapochromism upon exposure to organic solvents. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|