Synthesis, Characterization, and Fluorescence Behavior of Twisted and Planar B<sub>2</sub>N<sub>2</sub>-Quaterphenyl Analogues
Bibliographic record
Abstract
A series of planar and twisted heteroaromatic quaterphenyl analogues containing BN ring linkages has been synthesized using primarily difunctional Lewis acidic diborabiphenyl moieties as molecular cores. Crystal structure analyses indicated the presence of large twist angles between adjacent aromatic rings in 1 and 3, which were also observed to possess nonfluorescent behavior due to a lack of molecular rigidity and insufficient B=N character in the excited state. In contrast, the incorporation of one or two bridging ethylene groups between the adjacent rings (installed via an ethynyl cycloisomerization) was found to afford planar phenanthrene or pyrene moieties, which resulted in weak fluorescence behavior (Phi F = 0.02-0.16) for the n-Bu and Ph derivatives 5-12. Emission colors ranged from green (lambda em = 521 nm) to red (lambda em = 630 nm) and depended primarily on the conformation (2,2'- vs 4,4'-), the extent of chromophore conjugation (phenanthrene vs pyrene), and the type of exocyclic substituent present (n-Bu vs Ph). Communication between the two phenanthrene or pyrene moieties was observed in some cases, which was characterized by bathochromically shifted emission bands relative to that of monomeric phenanthrene or pyrene species. Unique excited-state dimer (excimer) fluorescence was observed for the 2,2'-isomer 8, which was characterized by broad, low-energy emission bands bathochromically shifted from that of the corresponding monomer.
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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) | 0.000 | 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".