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Intermolecular Hydrogen-Bond-Assisted Solid-State Dual-Emission Molecules with Mechanical Force-Induced Enhanced
Xiaohui Wang1, Jianyu Zhang2, Xiaoyu Mao1
1Guangdong Provincial Key Laboratory of Information Photonics Technology, School of Material and Energy, Guangdong University of Technology, Guangzhou 510006, P. R. China.
The Journal of Organic Chemistry
|June 21, 2022
Summary
Novel pyrene derivatives with intermolecular hydrogen bonds exhibit enhanced solid-state blue emission. These materials show dual emission and improved luminescence under mechanical force, suitable for advanced applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Hydrogen bonds are vital in life sciences and materials science, influencing molecular properties and enabling high-tech applications.
- Pyrene-based compounds are explored for their luminescent properties, but achieving efficient solid-state emission with tunable characteristics remains a challenge.
Purpose of the Study:
- To develop novel pyrene-based intermediates and luminescent materials with enhanced solid-state dual-emission properties.
- To investigate the role of intermolecular hydrogen bonds in mechanical force-induced enhanced emission.
- To explore potential applications in organic electronics, bioimaging, and chemosensors.
Main Methods:
- Synthesis of pyrene-based intermediates (1,3,6,8-tetrabromo-2,7-dihydroxypyrene and 1,3,6,8-tetrabromo-2-hydroxypyrene) via hydroxylation and bromination.
- Pd-catalyzed coupling reactions to synthesize new pyrene-based luminescent materials (compounds 3-5).
- Characterization of photophysical properties, thermal stability, and response to mechanical force.
Main Results:
- Efficient synthesis of novel bromopyrene intermediates and luminescent materials with high thermal stability (336-447 °C) and blue emission (<463 nm).
- Compounds with specific substitutions (e.g., hydroxyl or methoxy groups) exhibited dual emission and mechanical force-induced enhanced emission due to hydrogen bonding.
- Demonstrated advantages including deeper blue emission, narrower full width at half-maximum, stronger steric effects, and higher hydrophilicity.
Conclusions:
- The developed pyrene-based materials offer efficient solid-state dual-emission with tunable properties influenced by intermolecular hydrogen bonds.
- Mechanical force can enhance luminescence in these materials, opening avenues for mechano-responsive devices.
- These novel materials hold significant potential for applications in organic electronics, bioimaging, and chemical sensing.
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