Annulated Azuleno[2,1,8‐<i>ija</i>]azulenes: Synthesis and Properties
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Bibliographic record
Abstract
Abstract Non‐alternant non‐benzenoid hydrocarbons exhibit very different optical and electronic properties than their well‐studied benzenoid analogues. However, preparing such structures with extended conjugation length, remains challenging. Herein, we report the synthesis and properties of azuleno[2,1,8‐ija]azulene derivatives using a two‐step sequence involving a four‐fold aldol condensation between aromatic dialdehydes and readily available tetrahydropentalene‐2,5‐(1 H ,3 H )‐dione. Molecules with band gap values ranging from 1.69 to 2.14 eV and molar extinction coefficients ( ϵ ) of nearly 3×10 5 M −1 cm −1 have been prepared. These annulene‐like structures exhibit significant diatropic ring currents (aromatic), as supported by 1 H NMR spectroscopy and DFT calculations. Field‐effect transistors (OFETs) using azuleno[2,1,8‐ija]azulene derivatives as semiconductors exhibit charge mobility values of up to 0.05 cm 2 V −1 s −1 .
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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) | 0.002 | 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.
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