Properties Research of Poly(vinyl alcohol) Phosphorescent Films Doped with 9-Fluorenyl Methoxycarbonyl-Tyrosine at Room Temperature

doi:10.6023/cjoc202409005

Abstract

Room temperature phosphorescent (RTP) materials have broad application prospects in information encryption, optical sensing, biological imaging, information storage and so on. However, the realization of long-lived, high-efficiency phosphorescence in organic materials at room temperature represents a challenge, largely because the phosphorescence emission of organic molecules under ambient conditions is often hindered by intensive non-radiative transitions, inefficient intersystem crossing, and quenching of oxygen. In this study, the doped polymer matrix strategy was mainly used to achieve long-life room temperature phosphorescence emission. Two kinds of 9-fluorenyl methoxycarbonyl (Fmoc)-Tyrosine@PVA films prepared can produce phosphorescence emission with a lifetime of more than 4000 ms and blue afterglow with a long duration of 41 s after irradiation by 275 nm ultraviolet light source. Furthermore, Rhodamine B, a dye molecule, was doped in the system to adjust the color of the doped films by Förster-resonance energy transfer process.

Key words: tyrosine, room temperature phosphorescence, polyvinyl alcohol, resonance energy transfer

Cite this article

Yulan Gao, Jiangqin Long, Qiusheng Wang. Properties Research of Poly(vinyl alcohol) Phosphorescent Films Doped with 9-Fluorenyl Methoxycarbonyl-Tyrosine at Room Temperature[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1261-1267.

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Fig. & Tab. 8

Figure 1. (a) Molecular structures of Fmoc-Tyrosine, (b) fluorescence/phosphorescence emission spectra, and (c) lifetime decay curves of Fmoc-Tyrs@PVA films

Compound	Fluorescence			Phosphorescence
Compound	λ_ex/nm	λ_em/nm	Ф_Fluo/%	λ_em/nm	τ/ms	Ф_Phos/%
Fmoc-D-Tyr	275	314	2.98	460	4248.33	15.37
Fmoc-L-Tyr	275	318	6.24	460	4256.54	16.89
Fmoc-D-Tyr/RhB	275	314/592	1.68	461/589	3387.85	18.56
Fmoc-L-Tyr/RhB	275	318/592	2.88	461/589	3127.54	22.66

Table 1. Test results of photophysical properties of Fmoc-D-Tyr@PVA, Fmoc-L-Tyr@PVA, Fmoc-D-Tyr/RhB@PVA, and Fmoc-L-Tyr/ RhB@PVA films

Figure 2. (a) Luminescence photograph at an excitation wavelength of 275 nm (UV irradiation time is 5 s), and (b) CIE coordinate diagram of Fmoc-Tyrs@PVA films

Figure 3. (a) Phosphorescence-excitation mapping, and (b) excitation-dependent delayed phosphorescence spectra of Fmoc-L-Tyr@PVA films

Figure 4. (a) 1H NMR spectra of 10 mg PVA, 5 mg Fmoc-L-Tyr and 5 mg Fmoc-L-Tyr＋10 mg PVA in 0.55 mL DMSO-d6; (b) 1H NMR spectra of 10 mg PVA, 5 mg Fmoc-D-Tyr and 5 mg Fmoc-D-Tyr＋10 mg PVA in 0.55 mL DMSO-d6

Figure 5. XRD patterns of PVA and Fmoc-Tyrs@PVA films

Figure 6. (a) Simplified Jablonski diagram to explain the phosphorescence energy transfer; (b) Phosphorescence emission spectra of Fmoc-Tyrs@PVA films and the UV absorption spectrum and fluorescence emission spectrum of RhB aqueous solution

Figure 7. (a) Phosphorescent emission spectra, (b) phosphorescent life decay curves, and (c) luminescent photograph of Fmoc- Tyr/RhB@PVA films at an excitation wavelength of 275 nm (UV irradiation time is 5 s)

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