Persistent Solid‐State Phosphorescence and Delayed Fluorescence at Room Temperature by a Twisted Hydrocarbon
Open accessAbstract
The dehydrating cyclotrimerization of 1‐tetralone in the presence of titanium tetrachloride at high temperatures leads to homotruxene, a nonplanar arene in which the twist angles between its three outer benzene rings and the central benzene are stabilized by ethylene bridges. This non‐planar configuration allows for pronounced spin–orbit coupling and a high triplet energy, leading to room‐temperature phosphorescence in air with a lifetime of 0.38 s and a quantum yield of 5.6 %, clearly visible to the human eye after switching off the excitation. Triplet–triplet annihilation is found to simultaneously lead to a substantial delayed fluorescence, unprecedented from a pure hydrocarbon at ambient conditions, with a lifetime of 0.11 s.
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Room-temperature phosphorescence from organic aggregates
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- Authors
- Salla, C. A. M., Farias, G., Rouzières, M., Dechambenoit, P., Durola, F., Bock, H., de Souza, B., & Bechtold, I. H.
- Affiliations
- Universidade Federal de Santa Catarina (BR)
- Centre National de la Recherche Scientifique (FR)
- Centre de Recherche Paul Pascal CNRS & Université de Bordeaux 115, av. Schweitzer 33600 Pessac France
- Departamento de Química Universidade Federal de Santa Catarina 88040-900 Florianópolis SC Brazil
- Corresponding author
- Bechtold, Ivan H.
- ORCID
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2019-04-10
- Volume
- 58
- Issue
- 21
- Pages
- 6982-6986
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2939001674
- Cited by
- 120
- References
- 32
- Citations by year
- 2026: 11 · 2025: 16 · 2024: 19 · 2023: 20 · 2022: 9 · 2021: 21 · 2020: 16 · 2019: 8
- FWCI
- 4.88
- Type
- journal article
- Language
- en
- Open access
- green
- zenodo.org
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion)
- Zenodo (CERN European Organization for Nuclear Research) (submittedVersion, cc-by)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Light-Emitting Diodes Research
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
- Keywords
- room-temperature phosphorescence, delayed fluorescence, titanium tetrachloride, spin-orbit coupling, triplet energy, triplet-triplet annihilation, ethylene bridge
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