ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Regioselective Fluorination of Acenes: Tailoring of Molecular Electronic Levels and Solid-State Properties.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed, 14 citations in OpenAlex.
- Efficient synthesis of fluorinated triphenylenes with enhanced arene-perfluoroarene interactions in columnar mesophases.Beilstein journal of organic chemistry · 2024Article
- Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof.Molecules (Basel, Switzerland) · 2023Article
- Shape control in 2D molecular nanosheets by tuning anisotropic intermolecular interactions and assembly kinetics.Nature communications · 2023Article
- Total Synthesis of the Antimycobacterial Natural Product Chlorflavonin and Analogs via a Late-Stage Ruthenium(II)-CatalyzedPharmaceuticals (Basel, Switzerland) · 2022Article
- Regioselective Fluorination of Acenes: Tailoring of Molecular Electronic Levels and Solid-State Properties.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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8 authors at 1 institution in 1 country.
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Abstract
Optoelectronic properties of molecular solids are important for organic electronic devices and are largely determined by the adopted molecular packing motifs. In this study, we analyzed such structure-property relationships for the partially regioselective fluorinated tetracenes 1,2,12-trifluorotetracene, 1,2,10,12-tetrafluorotetracene and 1,2,9,10,11-pentafluorotetracene that were further compared with tetracene and perfluoro-tetracene. Quantum chemical DFT calculations in combination with optical absorption spectroscopy data show that the frontier orbital energies are lowered with the degree of fluorination, while their optical gap is barely affected. However, the crystal structure changes from a herringbone packing motif of tetracene towards a planar stacking motif of the fluorinated tetracene derivatives, which is accompanied by the formation of excimers and leads to strongly red-shifted photoluminescence with larger lifetimes.
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