Exploring the Spatial Arrangement of <i>C</i><sub>s</sub>-Symmetric Boron Subphthalocyanine Hybrid Crystals by Tuning Arene–Perfluoroarene Interactions
Bibliographic record
Abstract
Manipulating the solid-state arrangements of organic electronic materials can profoundly impact the performance of the devices in which they are utilized. This study investigates how π–π interactions, notably arene-perfluoroarene (π H ···π F ) interactions, guide the crystal structures of boron subphthalocyanine (BsubPc) hybrid derivatives by leveraging the dual dipole moments inherent in F 8 BsubPcs and F 8 Bsub(Pc 2 –Nc 1 )s. We crafted a simple molecular design varying BsubPc-type hybrids by their axial moieties and number of peripheral arene sites while maintaining a consistent count of peripheral perfluoroarene (π–hole) sites. The geometric analyses revealed that solid-state arrangements of perfluorinated BsubPc-type hybrids can be purposefully altered by introducing substituents that promote π H ···π F stacking. We found that an additional fused benzene ring in the periphery introduced new stacking modes characterized by enhanced π–π overlap in F 8 Bsub(Pc 2 –Nc 1 ) hybrids compared to F 8 BsubPcs, producing one-dimensional slip-stacked columns directed by strong-to-moderate π H ···π F interactions. Incorporation of an axial phenol ligand in the F 8 Bsub(Pc 2 -Nc 1 ) architecture further directed new stacking patterns, transforming the framework of arene-perfluoroarene interactions from their axially halogenated counterparts. Long-range packing motifs, Hirshfeld surfaces, various solvent growth methods, serendipitous ring-opened structures, and halogen bonding were examined to understand these π H ···π F interactions further. This work realizes the control of BsubPc hybrid spatial arrangements through strategic π–π interactions and provides avenues for potentially improved electronic functionality via highly ordered close packing configurations.
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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 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 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".