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Record W2832618839 · doi:10.1002/ejoc.201801055

Synthesis of a Perylene Diimide Dimer with Pyrrolic N–H Bonds and N‐Functionalized Derivatives for Organic Field‐Effect Transistors and Organic Solar Cells

2018· article· en· W2832618839 on OpenAlex
Marcus Vespa, Jonathan Cann, Sergey Dayneko, Owen A. Melville, Arthur D. Hendsbee, Yingping Zou, Benoît H. Lessard, Gregory C. Welch

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2018
Typearticle
Languageen
FieldEngineering
TopicOrganic Electronics and Photovoltaics
Canadian institutionsUniversity of OttawaUniversity of Calgary
FundersNatural Sciences and Engineering Research Council of CanadaCanada First Research Excellence Fund
KeywordsPeryleneDiimideDimerChemistryOrganic solar cellSolar cellPhotochemistryDeprotonationPolymer chemistryOrganic chemistryMoleculePolymerMaterials science

Abstract

fetched live from OpenAlex

This study reports on the new and optimized synthesis of an N‐annulated perylene diimide dimer with functional N–H moieties. The presence of two N–H moieties renders the dimer relatively insoluble in most organic solvents. The dimer is easily functionalized with electron donating hexyl chains or electron withdrawing tert ‐butyloxycarbonyl (tBOC) groups to yield highly soluble materials. The tBOC groups can be thermally cleaved in the thin film to give the parent dimer. The N–H bonds are acidic and interact with volatile organic bases. Deprotonation results in a color change from red to blue. All compounds have utility as electron transport materials in organic field‐effect transistors and green solvent, air processed organic solar cells. Electron mobilities were on the order of about 2–7 × 10 –6 cm 2 /V s. Solar cell power conversion efficiency reached 2 % for those using the tBOC functionalized dimer, 3 % for those using the H‐atom functionalized dimer, and 6 % for those using the hexyl chain functionalized dimer. The performance of the latter is quite impressive considering the simple materials synthesis and greener solar cell processing.

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.

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)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation 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 score0.004
Threshold uncertainty score0.899

Codex and Gemma teacher scores by category

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)0.0010.000

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 head0.004
GPT teacher head0.170
Teacher spread0.167 · 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