Table · dataset · 2026
Dual-State Fluorescence with Efficiency Close to Unity from D‑π-A-Type Triarylborane-Based Naphthalenes
Listed in ZivaHub and Deakin Research Online — shown once because both records carry DOI 10.1021/acs.joc.6c00979.s001
Fluorophores exhibiting bright fluorescence in both dilute solution and the solid state, termed dual-state emission (DSE), are more attractive for practical applications than those that fluoresce in a single state.
Description
Herein, we disclose two DSE-active naphthalene derivatives, <b>BNPh-Nap</b> and <b>BNOPh-Nap</b>, featuring a simple D-π-A structure with an electron-accepting dimesitylboryl (BMes<sub>2</sub>) and electron-donating diphenylamino (NPh<sub>2</sub>) or <i>N</i>,<i>N</i>’-di(4-methoxyphenyl)amino (N<sup>OMe</sup>Ph<sub>2</sub>) substituents at the 2,6-positions of the naphthalene core unit.
Despite the very flat structure of the naphthalene core unit, the steric hindrance of the BMes<sub>2</sub> and diarylamino groups can effectively suppress intermolecular π-π interactions in the solid state. As a result, <b>BNPh-Nap</b> exhibits strong fluorescence not only in solution (Φ<sub>F</sub> = 0.97 in cyclohexane) but also in the solid state, including powder (Φ<sub>F</sub> = 0.67) and neat film (Φ<sub>F</sub> = 0.51).
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From <b>BNPh-Nap</b> to <b>BNOPh-Nap</b>, although the fluorescence efficiency decreases slightly in solution (Φ<sub>F</sub> = 0.71 in cyclohexane), the enhanced electron-donating ability of the amino group greatly boosts the solid-state fluorescence, yielding near-unity Φ<sub>F</sub> values in both powder (Φ<sub>F</sub> = 0.91) and film (Φ<sub>F</sub> = 0.99). These results demonstrate that simple modification of a conventional planar π-core with BMes<sub>2</sub> and diarylamino groups enables high-performance DSE without complex twisted architectures, providing an effective strategy for developing DSE-active fluorophores.
Links
Where it is published
- DOI doi.org/10.1021/acs.joc.6c00979.s001 ↗
DOI / persistent id · from zivahub uct ac za
Catalogue records · 1
- OAI-PMH record api.figshare.com/v2/oai?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Af… ↗
metadata API · from zivahub uct ac za
Topics
- From keywords
- Astronomy & Astrophysics · Astronomy & Astrophysics · Chemistry · Chemistry · Earth & Environmental Science · Earth & Environmental Science · Medicine & Health · Medicine & Health
- Inferred from text
- Medicinal and biomolecular chemistry 70%
Provenance · 2 source records, 14 field assertions
| Source | Key | Last seen | Raw |
|---|---|---|---|
| ZivaHub | oai:figshare.com:article/34031227 | 13 d ago | JSON v1 |
| Deakin Research Online | oai:figshare.com:article/34031227 | 13 d ago | JSON v1 |
| Field | Assertion | Extractor | Evidence |
|---|---|---|---|
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| concepts[field].local:field:astronomy | mapping · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| concepts[field].local:field:astronomy | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
| concepts[field].local:field:chemistry | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
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| concepts[field].local:field:earth-environmental | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
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| concepts[field].local:field:medicine-health | mapping · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| concepts[field].local:field:medicine-health | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
| description | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | /metadata/dc/description |
| license | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | /metadata/dc/rights |
| publication_date | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| title | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | /metadata/dc/title |