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Record W2316229608 · doi:10.1021/ie202998f

One Well-Placed Methyl Group Increases the Solubility of Phenoxy Boronsubphthalocyanine Two Orders of Magnitude

2012· article· en· W2316229608 on OpenAlexafffund
Andrew S. Paton, Alan J. Lough, Timothy P. Bender

Bibliographic record

VenueIndustrial & Engineering Chemistry Research · 2012
Typearticle
Languageen
FieldMaterials Science
TopicPorphyrin and Phthalocyanine Chemistry
Canadian institutionsUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of CanadaOntario Centres of Excellence
KeywordsSolubilityAlkylGroup (periodic table)ChemistryArgument (complex analysis)MoleculeCrystal (programming language)Derivative (finance)Symmetry (geometry)Computational chemistryMaterials scienceOrganic chemistryMathematicsComputer science

Abstract

fetched live from OpenAlex

Boronsubphthalocyanine ( BsubPc ) derivatives are materials that have recently seen an increase in attention, particularily for application as colorants and functional materials in organic electronic devices. However, the solubilities of most BsubPc derivatives are too low to utilize solution-based processing techniques. Where there are derivatives that are soluble, they rely on the addition of large alkyl chains for solubilization the result of which is an increase in the molecular weight and a decrease of the specific absorptivity of the BsubPc . In this paper we disclose the identity of two mass-efficient, highly soluble BsubPc derivatives: 3-methylphenoxy- BsubPc and 3,4-dimethylphenoxy- BsubPc . We compare their solubilities and crystal packing structures to previously known BsubPc derivatives. We put forward a symmetry-based argument for the reason for their surprisingly high solubility wherein we treat the molecules as two separate fragments: the phenoxy group and the BsubPc group. The symmetry-based argument suggests that by ignoring the BsubPc fragment common to each derivative a better estimate of the relative solubilities can be estimated through previously established empirical formulas.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.003
Threshold uncertainty score0.009

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0030.000

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.

Opus teacher head0.103
GPT teacher head0.340
Teacher spread0.237 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

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".

Quick stats

Citations29
Published2012
Admission routes2
Has abstractyes

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Same venueIndustrial & Engineering Chemistry ResearchSame topicPorphyrin and Phthalocyanine ChemistryFrench-language works237,207