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Record W4413102074 · doi:10.1021/acsomega.5c04003

Confirmation of Microwave-Assisted Synthesis of Chloro-Boron Subphthalocyanines and Chloro-Boron Subnaphthalocyanines with Rapid Screening and Data Acquisition via HPLC-PDA

2025· article· en· W4413102074 on OpenAlexafffund
Lili Zhang, Xinyue Ma, Ishita Aggarwal, Nina F. Farac, Aleksa Dovijarski, Timothy P. Bender

Bibliographic record

VenueACS Omega · 2025
Typearticle
Languageen
FieldMaterials Science
TopicPorphyrin and Phthalocyanine Chemistry
Canadian institutionsUniversity of New BrunswickUniversity of Toronto
FundersHatchNatural Sciences and Engineering Research Council of CanadaGovernment of Ontario
KeywordsBoronMicrowaveHigh-performance liquid chromatographyChromatographyChemistryMaterials scienceOrganic chemistryComputer scienceTelecommunications

Abstract

fetched live from OpenAlex

High Resolution Image Download MS PowerPoint Slide Herein, we report an investigation into the use of a scientific microwave reactor for the synthesis of chloro-boron subphthalocyanines (Cl-BsubPcs), its derivatives, and the π-extended alternative called chloro-boron subnaphthalocyanine (Cl–Cl n BsubNc). Reaction optimization screening is presented with the aid of a high-pressure liquid chromatography system equipped with a photodiode array detector (HPLC-PDA) and used for quantitative analysis to calculate the conversion of phthalonitriles and 2,3-dicyanonaphthalene to the Cl-BsubPcs and Cl–Cl n BsubNcs, respectively, by leveraging the characteristic UV–vis absorbance profiles of the Cl-BsubPcs and Cl–Cl n BsubNcs. The microwave reaction process was found to reduce the reaction time from multiple hours to 5 to 36 min, reducing the overall time needed for the synthesis of the desired compounds, and provided a streamlined process of optimizing the synthesis of peripherally and axially substituted Cl-BsubPc derivatives. With enhanced heating, difficult-to-synthesize Cl–Cl 12 BsubPc was found to achieve moderate conversion through multiple microwave irradiation cycles. With this streamlined process, the lack of ethereal cleavage of aryl–aryl ether moieties (i.e., p -tolyl group) attached to the periphery of a Cl-BsubPc was achieved and is also presented. Although random bay halogenation of Cl-BsubNc was not found to be suppressed under the reaction conditions in the microwave, we present the microwave synthesis of Cl–Cl n BsubNcs while tracking random bay halogenation production using HPLC-PDA and confirm their characterization via mass spectrometry.

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 distilled prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
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 score0.050
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.001
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

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 head0.019
GPT teacher head0.261
Teacher spread0.242 · 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 teacher head, not a consensus.

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

Citations3
Published2025
Admission routes2
Has abstractyes

Explore more

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