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Near-Infrared Emission by Tuned Aggregation of a Porphyrin Compound in a Host–Guest Light-Emitting Electrochemical Cell

Mone, Mariza ; Tang, Shi ; Genene, Zewdneh ; Murto, Petri ; Jevric, Martyn ; Zou, Xianshao LU ; Ràfols-Ribé, Joan ; Abdulahi, Birhan A. ; Wang, Jia and Mammo, Wendimagegn , et al. (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.

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organization
publishing date
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}},
}