Microwave Synthesis of Thionated Naphthalene Diimide-Based Small Molecules and Polymers
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Bibliographic record
Abstract
Thionated naphthalene diimides (NDIs) are promising materials for n-type organic semiconductors; despite their potential, synthetic routes to thionated NDIs are generally lengthy, nonselective, and low yielding and their polymeric analogues have yet to be reported in the literature. Here, we describe the rapid and selective thionation of thiophene- and selenophene-flanked NDIs using microwave irradiation and excess Lawesson's reagent. Remarkably, >99% conversion to the trans-dithionated product is observed by NMR within 45 min. Steric effects imparted by NDI core substituents prevent excess thionation, simplifying purification procedures. We apply this methodology to the postpolymerization thionation of NDI-based polymers to afford a series of polymers with varying degrees of thionation. Thionated NDIs exhibit bathochromic shifts of up to ∼100 nm in localized absorption maxima and increased electron affinities.
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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 | 0.001 | 0.001 |
| 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 | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
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Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
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