Donor or Acceptor? How Selection of the Rylene Imide End Cap Impacts the Polarity of π-Conjugated Molecules for Organic Electronics
Bibliographic record
Abstract
Three molecular semiconductors are compared and evaluated in organic field-effect transistors and organic solar cells. The molecules are constructed from the dyes diketopyrrolopyrrole (DPP), perylene diimide (PDI), and N -(alkyl)benzothioxanthene-3,4-dicarboximide (BTXI). The compound PDI–DPP–PDI ( 1 ) has previously been reported and used as a nonfullerene acceptor. The compounds PDI–DPP–BTXI ( 2 ) and BTXI–DPP–BTXI ( 3 ) were synthesized using direct (hetero)arylation methods and fully identified using NMR spectroscopy and mass spectrometry. All three compounds were characterized using UV–visible spectroscopy, cyclic voltammetry, and density functional theory calculations. Increasing the BTXI content results in a progressive destabilization of the electronic energy levels. For all compounds, no significant changes in the optical absorption spectra are observed when compared to a combination of the constituent optical absorption spectra. Compound 1 exhibits electron transport characteristics and functions as an electron acceptor in solar cells that produce a power conversion efficiency of 5%. Compound 2 exhibits unbalanced (electron transporting dominate) ambipolar charge transport characteristics and performs better as a nonfullerene acceptor in solar cells. Compound 3 exhibits balanced ambipolar charge transport characteristics and performs best as a donor in solar cell devices. The ability to tune the optical and charge-carrier transport characteristics of these panchromatic dyes through direct (hetero)arylation synthesis offers a distinctive way to create organic semiconductors that span a range of device performance metrics.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| 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 | 0.001 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.002 | 0.001 |
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 itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".