Synthesis of polycyclic aromatic hydrocarbon containing cyclophanes: new and improved methodologies
Bibliographic record
Abstract
Cyclophanes are a vast class of compounds that can be defined as any system containing an aromatic system bridged by at least one n-membered bridge (n≥0). This description encompasses a large number of compounds, but relatively few examples in which the aromatic system is more complex than benzene exist. This is largely due to the increase is synthetic difficulty and a lack of universal methodologies. The work described in this thesis includes improvements in the synthesis of pyrenophanes and the introduction of new methodology for cyclophane formation in which the aromatic unit is peropyrene. Chapter 1 serves as an introduction to the concept of non-planarity in aromatic systems and the strategies for incorporating such morphologies into structures. Focus has been placed primarily on cyclophanes containing one aromatic system and one bridge and their advantages in structural modulation. Chapter 2 contains a review of the history of pyrenophanes and strategies towards their preparation. Improvements to the synthesis of the 1,n-dioxa-[n](2,7)pyrenophanes and [n](2,7)pyrenophanes are discussed in detail. Additionally, the reactivity of these systems is briefly discussed. Chapter 3 introduces peropyrene and discusses its properties and limited synthetic accessibility. The synthesis of a series of new cyclophanes is discussed which takes advantage of the dimerization of phenalenlyl radicals generated phenalene. Characterization of resulting [n](2,6)peropyrenophanes is briefly discussed.
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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 | 0.000 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.003 | 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".