Spectral Properties of Fluorophores Combining the Boronic Acid Group with Electron Donor or Withdrawing Groups. Implication in the Development of Fluorescence Probes for Saccharides
Bibliographic record
Abstract
We evaluated the spectral properties of four stilbene derivatives containing the boronic acid group [−B(OH) 2 ]:stilbene-4-boronic acid (STBA), 4‘-cyanostilbene-4-boronic acid (CSTBA), 4‘-methoxystilbene-4-boronic acid (MSTBA), and 4‘-(dimethylamino)stilbene-4-boronic acid (DSTBA). The emission spectrum of DSTBA displays a large solvent-polarity dependence showing the formation of a photoinduced charge transfer state (CT). This state is weakly present in MSTBA and not present for CSTBA and STBA for the neutral form of the boronic acid group. These results show the donor withdrawing property of the neutral form of the boronic acid group. At higher pH, the boronic acid group is present in the anionic form [−B(OH) 3 - ], resulting in a change of the configuration around the boron atom from the triangular planar (sp 2 hybridization) to the tetrahedral conformation (sp 3 hybridization). This change induced a blue shift of about 50 nm and an increase of intensity in the emission spectrum of DSTBA because of the loss of the electron-withdrawing properties for the anionic form of the boronic acid group, leading to the loss of the CT effect. The same effect is also observed for MSTBA. In contrast, a red shift of about 35 nm and a decrease of intensity are observed for CSTBA from the neutral to the anionic forms of the boronic acid group. These observations lead to the conclusion that the anionic form of the boronic acid group acts as an electron donor group and a photoinduced CT state can be formed when an electron withdrawing group is present on the fluorophore. The usefulness of this effect for the development of saccharide probes is also demonstrated. After addition of sugar, the emission spectra of DSTBA and MSTBA showed a blue shift and an increase of the intensity. On the other hand, a red shift and a decrease of the intensity are observed in the emission spectra of CSTBA after addition of sugar. A change from the neutral to the anionic form of the boronic acid group is used to explain these changes. These results show that the use of the combination of electron donor or withdrawing groups with the boronic acid group is a new and promising way to develop ratiometric fluorescent probes for glucose and other saccharides.
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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 | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 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".