TIPS-anthracene: a singlet fission or triplet fusion material?

Pun, Jack Ka Hei; Gallaher, Joseph K.; Frazer, Laszlo; Prasad, Shyamal K. K.; Dover, Cameron B.; MacQueen, Rowan W.; Schmidt, Timothy W.

doi:10.1117/1.jpe.8.022006

Cited by 17 publications

(17 citation statements)

References 32 publications

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“…23 Moreover, a recent report on 9,10-bis(TIPS)anthracene aggregates in solution showed only modest SF yields. 24 Crystalline BPEA powder obtained from Sigma-Aldrich contains 59.90 ± 0.02% C2/c and 40.10 ± 0.02% Pbcn polymorphs ( Figure 1a) based on a quantitative powder X-ray diff raction (PXRD) analysis ( Figure S1). 17 BPEA films were prepared by thermal vapor deposition under high vacuum onto a sapphire substrate followed by two annealing methods: solvent vapor annealing with dichloromethane for 12 h or thermal annealing at 120 °C for 3 h. Samples for PXRD analysis were scraped off the annealed films to remove preferred orientations.…”

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confidence: 99%

Singlet Fission in 9,10-Bis(phenylethynyl)anthracene Thin Films

et al. 2018

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Singlet fission (SF) in two or more electronically coupled organic chromophores converts a high-energy singlet exciton into two low-energy triplet excitons, which can be used to increase solar cell efficiency. Many known SF chromophores are unsuitable for device applications due to chemical instability and low triplet state energies. The results described here show that efficient SF occurs in polycrystalline thin films of 9,10bis(phenylethynyl)anthracene (BPEA), a commercial dye that has singlet and triplet energies of 2.40 and 1.11 eV, respectively, in the solid state. BPEA crystallizes into two polymorphs with space groups C2/c and Pbcn, which undergo SF with kSFA = (109 ± 4 ps) −1 and kSFB = (490 ± 10 ps) −1 , respectively. The high triplet energy and efficient SF evidenced from the 180 ± 20% triplet yield make BPEA a promising candidate for enhancing solar cell performance.

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confidence: 99%

Singlet Fission in 9,10-Bis(phenylethynyl)anthracene Thin Films

et al. 2018

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“…TIPS-Ac possesses S 1 energy of 2.78 eV, which was estimated with extrapolation of the absorption spectrum, and emission with peaks at 430 nm (0-0), 470 nm (0-1), and 500nm (0-2). [25][26][27][28][29] The photoluminescence quantum yield (PLQY) of a 1 mM TIPS-Ac toluene solution was measured to be 75 ± 2 %, when excited at 405nm. 30 We begin by investigating the TTA properties of TIPS-Ac, using a conventional sensitization process.…”

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confidence: 99%

Photon Upconversion from Near-Infrared to Blue Light with TIPS-Anthracene as an Efficient Triplet–Triplet Annihilator

Nishimura

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et al. 2019

ACS Materials Lett.

109

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Photon upconversion (PUC) via triplet-triplet annihilation (TTA) from near-infrared (NIR) to blue photons could have important applications especially to bio-imaging and drug delivery accompanied by photochemical reaction. The fundamental challenges in achieving this has been the large anti-Stokes shift combined with the need to efficiently sensitize within the biological transparency window (700-900 nm). This calls for materials combinations with minimal energy losses during sensitization and minimal energy requirements to drive efficient TTA. Here, we demonstrate efficient PUC converting from NIR energy to blue photons using the commercially available material 9,10-Bis[(triisopropylsilyl)ethynyl]anthracene (TIPS-Ac) as the annihilator. With a conventional triplet sensitizing system, TIPS-Ac performed TTA efficiency of 77 ± 3 % despite a relatively small driving force, compared to conventional TTA material converting from NIR to blue, for the TTA of less than 0.32 eV. Combined with Pt(II) meso-Tetraphenyl Tetrabenzoporphine (PtTPBP), which is a heavy atom triplet sensitizer that directly generates triplets upon NIR photon excitation, the resulting system allowed for an anti-Stokes shift of 1.03 eV. Our results highlight the use of direct triplet generation via NIR excitation as a useful path to achieving large anti-Stokes shift and also show that high TTA efficiencies can be achieved even in the absence of large driving energies for the TTA process.

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“…All these properties have been demonstrated separately in experiments, but not simultaneously. 43,44 . The decay rate can be as low as 90 s − 1 31,39,45 .…”

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confidence: 99%