Synthesis, Self-Assembly, and Solar Cell Performance of N-Annulated Perylene Diimide Non-Fullerene Acceptors
Why this work is in the frame
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Bibliographic record
Abstract
The synthesis, characterization, and photovoltaic performance of a series of N-annulated PDI materials is presented. Four novel N-annulated PDI compounds are reported, each of which can be synthesized in gram scale without the need for purification using column chromatography. N-Annulation of the PDI chromophore results in a decrease in electron affinity and lowering of the ionization potential, and renders the chromophore insoluble in organic solvents. Installation of an alkyl group improves the solubility. Single crystal X-ray analysis reveals a bowing of the aromatic backbone and compression of phenyl rings adjacent to the N atom. A brominated N-annulated PDI derivate represents a valuable synthon for creating novel multi-PDI chromophore materials. To demonstrate the utility of the new synthon for making electron transporting materials, a dimerization strategy was employed to create a dimeric PDI material. The PDI dimer has excellent solubility and film forming ability along with energetically deep HOMO and LUMO energy levels. X-ray crystal structure analysis reveals that, despite the isotropic nature of the molecule, only 1-D charge transport pathways are formed. Solar cells based on the new PDI dimer with the standard donor polymer PTB7 gave a high power conversion efficiency of 2.21% for this system. Through N -alkyl chain modification this PCE was increased to 3.13%. Further increases in PCE to 5.54% and 7.55% were achieved by using the more advanced donor polymers PTB7-Th and P3TEA, respectively. The simple yet high performance devices coupled with the highly modular and scalable “acceptor” synthesis make fullerene-free organic solar cells an attractive and cost-effective clean energy technology.
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Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it