Competing forces in the self-assembly of amide-functionalized discotic mesogens
Bibliographic record
Abstract
The effect of incorporating a single amide group on the self-assembly of discotic mesogens was examined. Two series of tetraalkoxydibenzophenazines amides were prepared: tertiary diethyl amides, dEt(n) incapable of hydrogen bonding, and secondary amides HBu(n) that can act as both H-bond donors and acceptors. These compounds exhibit markedly different behavior in solution; NMR studies of dEt(n) show no evidence of self-association, whereas HBu(n) strongly associate via H-bonding and π-stacking. Compounds HBu(n) also act as small molecule gelators in a range of solvents, a property not observed for the corresponding tertiary amides. All compounds were found to form Colh liquid crystal phases; variable temperature XRD experiments indicate that each column has a diameter approximately equal to that of a single molecule. A comparison of the phase behavior of HBu(n) and dEt(n) suggests that the columnar phases of the former are stabilized by hydrogen bonding, likely at the expense of local parallel alignment of these molecules. Single crystal X-ray diffraction studies revealed that dEt(6) adopts an antiparallel arrangement in the solid state, in keeping with previous theories of packing within columnar LC phases. These studies highlight the interplay between competing factors, such as hydrogen bonding, π-stacking and dipole-dipole interactions that affect the stability of the LC phases.
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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 | 0.000 |
| 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 | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.005 | 0.003 |
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; both teacher heads agree on what is shown here.
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".