Mechanism Landscape in Pyrylium Induced Organic Afterglow Systems

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2023 Aug 4

PMID 37538825

Authors

Guangming Wang

Xuefeng Chen

Xun Li

Ying Zeng

Kaka Zhang

Affiliations

Soon will be listed here.

Abstract

Manipulation of excited states and their dynamics represents a central topic in luminescence systems. We report an unexpected emergence of a high-performance organic afterglow in pyrylium induced photopolymerization systems, as well as the establishment of the mechanism landscape of the afterglow systems as a function of monomer types. In the case of methyl methacrylate, after pyrylium-catalyzed photopolymerization, the obtained materials exhibit a TADF-type organic afterglow with an afterglow efficiency of 70.4%. By using heavy-atom-containing methacrylate, the external heavy atom effect speeds up phosphorescence decay and switches on room-temperature phosphorescence in pyrylium-polymer systems. When 9-vinylcarbazole is used, the resultant materials display organic long persistent luminescence with hour-long durations and emission maxima around 650 nm. The intriguing mechanism landscape reflects the delicate balance of multiple photophysical processes in the pyrylium induced organic afterglow systems, which has been rarely explored in the reported studies.

Citing Articles

Room-temperature phosphorescent transparent wood.

Piao X, Wang T, Chen X, Wang G, Zhai X, Zhang K Nat Commun. 2025; 16(1):868.

PMID: 39833198 PMC: 11747176. DOI: 10.1038/s41467-025-55990-z.

References

Wang X, Sun Y, Wang G, Li J, Li X, Zhang K . TADF-Type Organic Afterglow. Angew Chem Int Ed Engl. 2021; 60(31):17138-17147. DOI: 10.1002/anie.202105628. View

Noda H, Chen X, Nakanotani H, Hosokai T, Miyajima M, Notsuka N . Critical role of intermediate electronic states for spin-flip processes in charge-transfer-type organic molecules with multiple donors and acceptors. Nat Mater. 2019; 18(10):1084-1090. DOI: 10.1038/s41563-019-0465-6. View

Zhang G, Palmer G, Dewhirst M, Fraser C . A dual-emissive-materials design concept enables tumour hypoxia imaging. Nat Mater. 2009; 8(9):747-51. PMC: 2846459. DOI: 10.1038/nmat2509. View

Wong M, Zysman-Colman E . Purely Organic Thermally Activated Delayed Fluorescence Materials for Organic Light-Emitting Diodes. Adv Mater. 2017; 29(22). DOI: 10.1002/adma.201605444. View

Ma X, Liu Y . Supramolecular Purely Organic Room-Temperature Phosphorescence. Acc Chem Res. 2021; 54(17):3403-3414. DOI: 10.1021/acs.accounts.1c00336. View

Chen B, Huang W, Nie X, Liao F, Miao H, Zhang X . An Organic Host-Guest System Producing Room-Temperature Phosphorescence at the Parts-Per-Billion Level. Angew Chem Int Ed Engl. 2021; 60(31):16970-16973. DOI: 10.1002/anie.202106204. View

Santos W, Budkina D, Santagneli S, Tarnovsky A, Zukerman-Schpector J, Ribeiro S . Ion-Pair Complexes of Pyrylium and Tetraarylborate as New Host-Guest Dyes: Photoinduced Electron Transfer Promoting Radical Polymerization. J Phys Chem A. 2019; 123(34):7374-7383. DOI: 10.1021/acs.jpca.9b03581. View

He Z, Gao H, Zhang S, Zheng S, Wang Y, Zhao Z . Achieving Persistent, Efficient, and Robust Room-Temperature Phosphorescence from Pure Organics for Versatile Applications. Adv Mater. 2019; 31(18):e1807222. DOI: 10.1002/adma.201807222. View

Kenry , Chen C, Liu B . Enhancing the performance of pure organic room-temperature phosphorescent luminophores. Nat Commun. 2019; 10(1):2111. PMC: 6506551. DOI: 10.1038/s41467-019-10033-2. View

10.

Li Q, Li Z . Molecular Packing: Another Key Point for the Performance of Organic and Polymeric Optoelectronic Materials. Acc Chem Res. 2020; 53(4):962-973. DOI: 10.1021/acs.accounts.0c00060. View

11.

Chen C, Chi Z, Chong K, Batsanov A, Yang Z, Mao Z . Carbazole isomers induce ultralong organic phosphorescence. Nat Mater. 2020; 20(2):175-180. DOI: 10.1038/s41563-020-0797-2. View

12.

Yin Zhang K, Yu Q, Wei H, Liu S, Zhao Q, Huang W . Long-Lived Emissive Probes for Time-Resolved Photoluminescence Bioimaging and Biosensing. Chem Rev. 2018; 118(4):1770-1839. DOI: 10.1021/acs.chemrev.7b00425. View

13.

Montes-Navajas P, Garcia H . Influence of CB[n] complexation on the quenching of 2,4,6-triphenylpyrylium excited states by Fe2+ ions. J Colloid Interface Sci. 2013; 410:111-5. DOI: 10.1016/j.jcis.2013.08.016. View

14.

Bhattacharjee I, Hirata S . Highly Efficient Persistent Room-Temperature Phosphorescence from Heavy Atom-Free Molecules Triggered by Hidden Long Phosphorescent Antenna. Adv Mater. 2020; 32(31):e2001348. DOI: 10.1002/adma.202001348. View

15.

Yang Z, Xu C, Li W, Mao Z, Ge X, Huang Q . Boosting the Quantum Efficiency of Ultralong Organic Phosphorescence up to 52 % via Intramolecular Halogen Bonding. Angew Chem Int Ed Engl. 2020; 59(40):17451-17455. DOI: 10.1002/anie.202007343. View

16.

Lin Z, Kabe R, Nishimura N, Jinnai K, Adachi C . Organic Long-Persistent Luminescence from a Flexible and Transparent Doped Polymer. Adv Mater. 2019; 30(45):e1803713. DOI: 10.1002/adma.201803713. View

17.

Zhang T, Ma X, Wu H, Zhu L, Zhao Y, Tian H . Molecular Engineering for Metal-Free Amorphous Materials with Room-Temperature Phosphorescence. Angew Chem Int Ed Engl. 2019; 59(28):11206-11216. DOI: 10.1002/anie.201915433. View

18.

Jinnai K, Kabe R, Lin Z, Adachi C . Organic long-persistent luminescence stimulated by visible light in p-type systems based on organic photoredox catalyst dopants. Nat Mater. 2021; 21(3):338-344. DOI: 10.1038/s41563-021-01150-9. View

19.

Samanta P, Kim D, Coropceanu V, Bredas J . Up-Conversion Intersystem Crossing Rates in Organic Emitters for Thermally Activated Delayed Fluorescence: Impact of the Nature of Singlet vs Triplet Excited States. J Am Chem Soc. 2017; 139(11):4042-4051. DOI: 10.1021/jacs.6b12124. View

20.

Zhang Y, Su Y, Wu H, Wang Z, Wang C, Zheng Y . Large-Area, Flexible, Transparent, and Long-Lived Polymer-Based Phosphorescence Films. J Am Chem Soc. 2021; 143(34):13675-13685. DOI: 10.1021/jacs.1c05213. View