Directed Metalation-Cross Coupling Route to Ferroelectric Liquid Crystals with a Chiral Fluorenol Core: The Effect of Intermolecular Hydrogen Bonding on Polar Order
Bibliographic record
Abstract
The chiral fluorenol mesogen ( R )-2-(1-octyloxy)-7-((4-undecyloxybenzoyl)oxy)fluoren-9-ol (( R )- 3 ) was synthesized using a combined directed metalation-cross coupling strategy. The SmC* liquid crystal phase formed by the fluorenol mesogen is more stable and has a wider temperature range than that formed by the fluorenone presursor, which may be ascribed to intermolecular hydrogen bonding. The spontaneous polarization ( P S ) of ( R )- 3 at 10 K below the SmC*-I phase transition temperature is −10.7 nC/cm 2 . Molecular modeling based on the Boulder model suggests that the intrinsic conformational bias favoring one orientation of the fluorenol dipole moment along the polar axis of the SmC* phase is very subtle and implies that self-assembly via hydrogen bonding may play a role in enhancing polar order. Results from FT-IR spectroscopy, dilution with achiral SmC additives, and deuterium exchange experiments suggest that the spontaneous polarization is enhanced by the formation of fluorenol dimers via OH−O C hydrogen bonding. Such self-assembly should increase the rotational order about the long molecular axis and, therefore, the orientational bias of the fluorenol transverse dipole moment along the polar axis that gives rise to P S .
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How this classification was reachedexpand
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 | 0.001 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 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)
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 teacher head, 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".