Near-Infrared Emission by Tuned Aggregation of a Porphyrin Compound in a Host–Guest Light-Emitting Electrochemical Cell
(2021) In Advanced Optical Materials 9(6).- Abstract
The synthesis of 5,10,15,20-tetrakis((5,10-bis((2-hexyldecyl)oxy)dithieno[3,2-c:3′,2′-h][1,5]naphthyridin-2-yl)ethynyl)porphyrin zinc(II) (Por4NT), a near-infrared (NIR) emitting compound, comprising a zinc porphyrin core linked with triple bonds through its meso positions to four 5,10-bis((2-hexyldecyl)oxy)dithieno[3,2-c:3′,2′-h][1,5]naphthyridine (NT) arms is reported. Por4NT featured high solubility in common non-polar solvents, which is ideal for easy processing through solution techniques, and high photoluminescence (PL) efficiency of ≈30% in dilute toluene solution. It also exhibited a strong tendency for aggregation because of its flat conformation, and this aggregation resulted in a strong redshifted emission and a drop in PL... (More)
The synthesis of 5,10,15,20-tetrakis((5,10-bis((2-hexyldecyl)oxy)dithieno[3,2-c:3′,2′-h][1,5]naphthyridin-2-yl)ethynyl)porphyrin zinc(II) (Por4NT), a near-infrared (NIR) emitting compound, comprising a zinc porphyrin core linked with triple bonds through its meso positions to four 5,10-bis((2-hexyldecyl)oxy)dithieno[3,2-c:3′,2′-h][1,5]naphthyridine (NT) arms is reported. Por4NT featured high solubility in common non-polar solvents, which is ideal for easy processing through solution techniques, and high photoluminescence (PL) efficiency of ≈30% in dilute toluene solution. It also exhibited a strong tendency for aggregation because of its flat conformation, and this aggregation resulted in a strong redshifted emission and a drop in PL efficiency. A well-matched PBDTSi-BDD-Py “host” terpolymer is therefore designed, which is capable of mitigating the aggregation of the Por4NT “guest”. An optimized blend of the host, guest, and an ionic-liquid electrolyte is utilized as the active material in a light-emitting electrochemical cell (LEC), which delivered strong NIR radiance of 134 µW cm-2 with a long wavelength maximum at 810 nm at a low drive voltage of 5.0 V. The attainment of the strong NIR emission from the host–guest LEC is attributed to a tuned aggregation of the Por4NT emitter, which resulted in the desired aggregation-induced redshift of the emission at a reasonably retained efficiency.
(Less)
- author
- organization
- publishing date
- 2021-01-14
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- aggregation, energy transfer, light-emitting electrochemical cells, near-infrared emission, porphyrins
- in
- Advanced Optical Materials
- volume
- 9
- issue
- 6
- article number
- 2001701
- publisher
- John Wiley & Sons Inc.
- external identifiers
-
- scopus:85099339703
- ISSN
- 2195-1071
- DOI
- 10.1002/adom.202001701
- language
- English
- LU publication?
- yes
- id
- 5a9542a6-9ebc-4bc5-812e-ce8056406271
- date added to LUP
- 2021-01-25 13:45:48
- date last changed
- 2023-11-20 22:02:18
@article{5a9542a6-9ebc-4bc5-812e-ce8056406271, abstract = {{<p>The synthesis of 5,10,15,20-tetrakis((5,10-bis((2-hexyldecyl)oxy)dithieno[3,2-c:3′,2′-h][1,5]naphthyridin-2-yl)ethynyl)porphyrin zinc(II) (Por4NT), a near-infrared (NIR) emitting compound, comprising a zinc porphyrin core linked with triple bonds through its meso positions to four 5,10-bis((2-hexyldecyl)oxy)dithieno[3,2-c:3′,2′-h][1,5]naphthyridine (NT) arms is reported. Por4NT featured high solubility in common non-polar solvents, which is ideal for easy processing through solution techniques, and high photoluminescence (PL) efficiency of ≈30% in dilute toluene solution. It also exhibited a strong tendency for aggregation because of its flat conformation, and this aggregation resulted in a strong redshifted emission and a drop in PL efficiency. A well-matched PBDTSi-BDD-Py “host” terpolymer is therefore designed, which is capable of mitigating the aggregation of the Por4NT “guest”. An optimized blend of the host, guest, and an ionic-liquid electrolyte is utilized as the active material in a light-emitting electrochemical cell (LEC), which delivered strong NIR radiance of 134 µW cm<sup>-2</sup> with a long wavelength maximum at 810 nm at a low drive voltage of 5.0 V. The attainment of the strong NIR emission from the host–guest LEC is attributed to a tuned aggregation of the Por4NT emitter, which resulted in the desired aggregation-induced redshift of the emission at a reasonably retained efficiency.</p>}}, author = {{Mone, Mariza and Tang, Shi and Genene, Zewdneh and Murto, Petri and Jevric, Martyn and Zou, Xianshao and Ràfols-Ribé, Joan and Abdulahi, Birhan A. and Wang, Jia and Mammo, Wendimagegn and Andersson, Mats R. and Edman, Ludvig and Wang, Ergang}}, issn = {{2195-1071}}, keywords = {{aggregation; energy transfer; light-emitting electrochemical cells; near-infrared emission; porphyrins}}, language = {{eng}}, month = {{01}}, number = {{6}}, publisher = {{John Wiley & Sons Inc.}}, series = {{Advanced Optical Materials}}, title = {{Near-Infrared Emission by Tuned Aggregation of a Porphyrin Compound in a Host–Guest Light-Emitting Electrochemical Cell}}, url = {{http://dx.doi.org/10.1002/adom.202001701}}, doi = {{10.1002/adom.202001701}}, volume = {{9}}, year = {{2021}}, }