Regioregular Phthalocyanines Substituted with Bulky Donors at Non‐Peripheral Positions
Bibliographic record
Abstract
Abstract Three regioregular phthalocyanines (1–3) were synthesized selectively by the cyclic tetramerization of phthalonitriles bearing a bulky diarylamine substituent at the next position of nitrile. The steric repulsion at the tetramerization of bulky phthalonitriles allowed for the selective formation of regioregular phthalocyanines as confirmed by NMR and single crystal X‐ray structural analyses. The absorption spectrum of 1 substituted with di(4‐tert‐butylphenyl)amine groups at the non‐peripheral positions showed a non‐split Q‐band at 764 nm, which was redshifted by 83 nm compared with that of metal free phthalocyanine (H2Pc). The TD‐DFT calculation and electrochemical studies prove that the substitution of diarylamine groups at the α‐positions effectively destabilizes the HOMO energy level, which causes a large redshift of the Q‐band. Moreover, 1 can generate a one‐electron oxidation species through chemical oxidation. The Q‐band position of 2 bearing 4,4′‐dimetoxyphenylamine units was further shifted by 10 nm compared with that of 1. In addition, 3 having carbazole units showed a small redshift of the Q‐band relative to H2Pc. The hole‐mobility of 2 in thin film was determined to be 1.1×10−5 cm V−1 s−1 by using a space charge limited current method. A perovskite solar cell employing 2 as a hole‐transporting layer gave an efficiency of 5.1 % under standard global 100 Wcm−2 AM 1.5 G illumination.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot 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.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 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 source (direct Gemma or distilled Codex), 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".