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| Main Authors: | , , , , |
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| Format: | Preprint |
| Published: |
2025
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| Subjects: | |
| Online Access: | https://arxiv.org/abs/2509.14417 |
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| _version_ | 1866914172207366144 |
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| author | Li, Wenlong Awuku, Stephen Merk, Jenna N. MacKinnon, Marc R. Stevens, Amy L. |
| author_facet | Li, Wenlong Awuku, Stephen Merk, Jenna N. MacKinnon, Marc R. Stevens, Amy L. |
| contents | Pyrene-functionalized materials are extensively employed in photoluminescent applications, owing to their extended π-conjugation and favorable photophysical properties. However, their luminescent performance is often attenuated by π-π stacking-driven excimer formation and molecular oxygen quenching. To mitigate these undesirable effects, a novel class of 7-tert-butylpyren-2-ol derivatives with extended 'arm-like' substituents at the 1,3-positions have been synthesized and their luminescent properties in solution have been thoroughly investigated. While the 2- and 7-positions of the pyrene core are frequently modified with hydroxyl and tert-butyl groups, this work presents the first introduction of 'arm-like' substituents at the 1,3-positions. The stretched-out 'arm-like' substituents not only introduce steric bulk to suppress excimer formation but also change the symmetry class of pyrene and modulate electron density at its 1,2,3,7-positions. These effects tune pyrene's energy levels and result in moderate (0.4) to high (0.7) fluorescence quantum yields and shorter-lived fluorescence lifetimes ranging from ca. 20 to 40 ns. These shorter lifetimes lead to a reduction of the pyrene derivatives' susceptibility to energy scavenging by molecular oxygen. In addition, the specific form of the 'arms' are important. Alkyl-containing arms and alkenyl-containing arms exhibit different decay pathways, which is reflected by their disparate nonradiative rates. Thus, the introduction of 'arm-like' modifications represents a promising approach to modulate the photophysical behaviour of an important class of polycyclic aromatic hydrocarbons, highlighting their applicability in next-generation electronic and optoelectronic systems. |
| format | Preprint |
| id |
arxiv_https___arxiv_org_abs_2509_14417 |
| institution | arXiv |
| publishDate | 2025 |
| record_format | arxiv |
| spellingShingle | Excimer-Suppressed and Oxygen-Tolerant Photophysics of 'Arm-like' Substituted Pyrene Derivatives Li, Wenlong Awuku, Stephen Merk, Jenna N. MacKinnon, Marc R. Stevens, Amy L. Chemical Physics Pyrene-functionalized materials are extensively employed in photoluminescent applications, owing to their extended π-conjugation and favorable photophysical properties. However, their luminescent performance is often attenuated by π-π stacking-driven excimer formation and molecular oxygen quenching. To mitigate these undesirable effects, a novel class of 7-tert-butylpyren-2-ol derivatives with extended 'arm-like' substituents at the 1,3-positions have been synthesized and their luminescent properties in solution have been thoroughly investigated. While the 2- and 7-positions of the pyrene core are frequently modified with hydroxyl and tert-butyl groups, this work presents the first introduction of 'arm-like' substituents at the 1,3-positions. The stretched-out 'arm-like' substituents not only introduce steric bulk to suppress excimer formation but also change the symmetry class of pyrene and modulate electron density at its 1,2,3,7-positions. These effects tune pyrene's energy levels and result in moderate (0.4) to high (0.7) fluorescence quantum yields and shorter-lived fluorescence lifetimes ranging from ca. 20 to 40 ns. These shorter lifetimes lead to a reduction of the pyrene derivatives' susceptibility to energy scavenging by molecular oxygen. In addition, the specific form of the 'arms' are important. Alkyl-containing arms and alkenyl-containing arms exhibit different decay pathways, which is reflected by their disparate nonradiative rates. Thus, the introduction of 'arm-like' modifications represents a promising approach to modulate the photophysical behaviour of an important class of polycyclic aromatic hydrocarbons, highlighting their applicability in next-generation electronic and optoelectronic systems. |
| title | Excimer-Suppressed and Oxygen-Tolerant Photophysics of 'Arm-like' Substituted Pyrene Derivatives |
| topic | Chemical Physics |
| url | https://arxiv.org/abs/2509.14417 |