Position of Methyl and Nitrogen on Axial Aryloxy Substituents Determines the Crystal Structure of Silicon Phthalocyanines
Bibliographic record
Abstract
Phthalocyanines are a class of organometallic compounds that have been investigated extensively for emerging applications such as organic photovoltaics, organic light-emitting diodes, and thin-film transistors. For these applications, the understanding of molecular structures and intermolecular interactions is extremely crucial and is one of the most promising pathways for designing a new generation of functional materials. Here, the crystal structures of six axially substituted silicon phthalocyanines (SiPcs) with aryloxy groups are reported. Three bis(methylphenoxy) SiPcs with varying methyl positions and two bis(pyridoxy) derivatives with varying nitrogen positions are compared to the bare bis(phenoxy) SiPc. Quantitative analysis is conducted to describe the impact of the position and nature of the functional group/atom on the orientation of the axial aryloxy subtituents as well as on the aromaticity and planarity of the SiPc macrocycle. Quantitative analysis of changes in intermolecular interactions, in particular, π–π interactions, and visual representation using Hirshfeld surfaces are also presented. In all cases, the axial aryloxy substituent determined the solid-state arrangement except for the bis(4-pyridoxy) SiPc, which is isostructural to bis(phenoxy) SiPc.
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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 | 0.000 | 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 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 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".