Synthesis and photophysical properties of donor-substituted phenyl-phosphachromones as potential TADF materials
- 5 February 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic Chemistry Frontiers
- Vol. 8 (8), 1747-1755
- https://doi.org/10.1039/d1qo00121c
Abstract
A series of novel arylamine-substituted phenyl-phosphachromones were constructed via post-functionalization. As a new type of D–π–A functional molecule, their photophysical properties can be well tuned by different amino substituents at different positions with variable Stokes shifts (Δλ = 127–299 nm). Moreover, compounds 4a, 4b, 4f, 4m, and 4n exhibit an unusual dual emission with a large wavelength difference. Strong intermolecular interactions were also observed for these compounds, and therein, a sandwich π(donor)–π(donor) stacking interaction was found in the solid-state structure of 4e. Moreover, (TD-)DFT computations were performed to rationalize the observed electronic properties and intramolecular interactions. Finally, the delayed fluorescence of these D–π–A molecules in the film was observed and further confirmed to be a result of thermally activated delayed fluorescence and mixed room-temperature phosphorescence.Keywords
Funding Information
- National Natural Science Foundation of China (21462019, 21676131)
- Jiangxi Provincial Department of Science and Technology (20143ACB20012)
- Education Department of Jiangxi Province (GJJ180625)
- Jiangxi Science and Technology Normal University (2018BSQD025)
This publication has 93 references indexed in Scilit:
- Luminescent distyrylbenzenes: tailoring molecular structure and crystalline morphologyJournal of Materials Chemistry C, 2013
- Benzofuran-fused Phosphole: Synthesis, Electronic, and Electroluminescence PropertiesOrganic Letters, 2013
- Bis(phosphoryl)‐Bridged Biphenyls by Radical Phosphanylation: Synthesis and Photophysical and Electrochemical PropertiesAngewandte Chemie, 2011
- Local Nature of Substituent Effects in Stacking InteractionsJournal of the American Chemical Society, 2011
- Thiophene-fused phospholo[3,2-b]phospholes and their dichalcogenides: Synthesis and structure–photophysical properties relationshipsComptes Rendus. Chimie, 2010
- Tunable Organophosphorus Dopants for Bright White Organic Light‐Emitting Diodes with Simple StructuresAdvanced Materials, 2009
- Superstructure‐Dependent Optical and Electrical Properties of an Unusual Face‐to‐Face, π‐Stacked, One‐Dimensional Assembly of Dehydrobenzo[12]annulene in the Crystalline StateChemistry – A European Journal, 2008
- First Examples of Organophosphorus-Containing Materials for Light-Emitting DiodesJournal of the American Chemical Society, 2003
- Self-Aggregation of Cationic Porphyrins in Water. Can π−π Stacking Interaction Overcome Electrostatic Repulsive Force?The Journal of Physical Chemistry A, 1997
- Manifestations of noncovalent interactions in the solid state. Dimeric and polymeric self-assembly in imidazolium salts via face-to-face cation—cation π-stackingSupramolecular Chemistry, 1993