Photothermal conversion performance of perylene diimide radical anion salts modified with tunable moieties

Li, Qizhe; Hou, Wenlong; Peng, Fei; Wang, Hailong; Zhang, Shuo; Dong, Danyang; Wu, Siyu; Zhang, Haiquan

doi:10.1007/s10853-018-2822-2

Cited by 13 publications

(12 citation statements)

References 31 publications

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“…Interestingly, there are several reports indicating PDI radical anion absorption in a similar wavelength region. With this wealth of information, we assigned this signal to the formation of PDI radical anion as a result of the PET process. − Our steady-state emission and theoretical studies already revealed the possibility of PET in the polar solvents.…”

Section: Resultsmentioning

confidence: 93%

Ultrafast Dynamics of Photoinduced Electron Transfer in Bay-Aryl-Substituted Perylene Diimide Derivatives

et al. 2022

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Blends of donors and acceptors have been widely used in bulk-heterojunction solar cells to have exciton formation and charge separation by photoinduced electron transfer (PET). In this work, we have synthesized perylene diimide (PDI)-based materials having different aryl substituents at the bay positions (4-Anisyl-PDI, CBZ-N-Ph-PDI, and 4-Pyridyl-PDI) to understand the excited-state dynamics of electron transfer. The detailed photophysics was studied using steady-state as well as ultrafast dynamics of the excited states in different solvents. CBZ-N-Ph-PDI showed tremendous effects of the solvent on the electronic properties compared with the other two derivatives. The emission quantum yield of CBZ-N-Ph-PDI decreases drastically in dichloromethane and other polar solvents, indicating strong electron transfer. DFT calculations showed that in CBZ-N-Ph-PDI the HOMO is centered mostly on the N-phenylcarbazole and the LUMO is on the electron-poor PDI moieties. In addition, the energy levels of the HOMO and HOMO−1 in CBZ-N-Ph-PDI are estimated to be identical. The free energy change for charge separation (ΔG CS ) was calculated using electrochemical and photophysical data and found to be negative for CBZ-N-Ph-PDI. The ground-and excitedstate dipole moment ratios suggest that the excited state of 4-Pyridyl-PDI (1.90) is less polar than that of 4-Anisyl-PDI (3.67), which provides an idea of the lower possibility of charge separation in 4-Anisyl-PDI and 4-Pyridyl-PDI. Ultrafast photodynamics studies of 4-Anisyl-PDI, CBZ-N-Ph-PDI, and 4-Pyridyl-PDI showed fast electron transfer only in CBZ-N-Ph-PDI and not in the other PDI derivatives. It was also observed that electron transfer is faster in DCM and THF than in toluene. Ultrafast dynamics studies showed the presence of an equilibrium between electron transfer and decay from the singlet excited state. Ultrafast studies also showed the features of the N-phenylcarbazole cation and PDI anion, further confirming the intramolecular electron transfer in CBZ-N-Ph-PDI.

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Section: Resultsmentioning

confidence: 93%

Ultrafast Dynamics of Photoinduced Electron Transfer in Bay-Aryl-Substituted Perylene Diimide Derivatives

et al. 2022

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“…To summarize, the photothermal conversion efficiency was tuned in the range of 23.7% to 47.9% for the PDI-PEI suspensions that have different yields of radical anions generated by varying the amounts of PEI doping. Note that the highest photothermal conversion efficiency of the unsubstituted PDI radical anion (47.9%) is comparable to that of functionalized perylene diimide radical anion salts (54.4%) with tetraphenoxy moieties onto the PDI cores and diisopropylbenzene in the amine position (TPPDI) (10 −4 M in DMF) ( Li et al, 2019 ). The efficiency is larger than a bola-form amphiphile PDI derivative’s radical anions (BPDI radical anion, 16.3%) and the supramolecule composed of BPDI and cucurbit [n]urils (CB [7]) free radical anion (BPDI/(CB [7]) 2 radical anion, 31.6%) ( Jiao et al, 2015 ).…”

Section: Resultsmentioning

confidence: 99%

Chemical doping of unsubstituted perylene diimide to create radical anions with enhanced stability and tunable photothermal conversion efficiency

et al. 2023

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N-doping of perylene diimides (PDIs) to create stable radical anions is significant for harvesting photothermal energy due to their intensive absorption in the near-infrared (NIR) region and non-fluorescence. In this work, a facile and straightforward method has been developed to control the doping of perylene diimide to create radical anions using organic polymer polyethyleneimine (PEI) as a dopant. It was demonstrated that PEI is an effective polymer-reducing agent for the n-doping of PDI toward the controllable generation of radical anions. In addition to the doping process, PEI could suppress the self-assembly aggregation and improve the stability of PDI radical anions. Tunable NIR photothermal conversion efficiency (maximum 47.9%) was also obtained from the radical-anion-rich PDI-PEI composites. This research provides a new strategy to tune the doping level of unsubstituted semiconductor molecules for varying yields of radical anions, suppressing aggregation, improving stability, and obtaining the highest radical anion-based performance.

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“…[16][17][18] The mechanism of these electron shuttle reactions is discussed controversially. [17][18][19][20][21][22] The observed photothermal conversion 23,24 implies that non-radiative relaxation processes are significant. This agrees with the observation that PBI radical anions tend to be non-fluorescent 15,23,25 like other radicals.…”

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confidence: 99%

Intersystem crossing of perylene bisimide neutral, radical anion, and dianion derivatives compared via ultrafast spectroelectrochemistry

Heitmüller¹,

Fröhlich²,

Renner³

et al. 2023

Phys. Chem. Chem. Phys.

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Photothermal conversion performance of perylene diimide radical anion salts modified with tunable moieties

Cited by 13 publications

References 31 publications

Ultrafast Dynamics of Photoinduced Electron Transfer in Bay-Aryl-Substituted Perylene Diimide Derivatives

Ultrafast Dynamics of Photoinduced Electron Transfer in Bay-Aryl-Substituted Perylene Diimide Derivatives

Chemical doping of unsubstituted perylene diimide to create radical anions with enhanced stability and tunable photothermal conversion efficiency

Intersystem crossing of perylene bisimide neutral, radical anion, and dianion derivatives compared via ultrafast spectroelectrochemistry

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