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Dual-State Fluorescence
with Efficiency Close to Unity
from D‑π-A-Type Triarylborane-Based Naphthalenes
Min Wang (21070)
Meng-Qi Wu (25143112)
Yi Fang (287944)
Cui-Hua Zhao (1447255)
Biophysics
Biochemistry
Space Science
Medicine
Biotechnology
Chemical Sciences not elsewhere classified
active naphthalene derivatives
naphthalene core unit
exhibits strong fluorescence
disclose two dse
conventional planar π
ome </ sup
f </ sub
nap </ b
2 </ sub
n </
active fluorophores
state fluorescence
dse ),
developing dse
‑ π
π interactions
yielding near
type triarylborane
steric hindrance
state emission
single state
results demonstrate
practical applications
efficiency close
effective strategy
donating diphenylamino
donating ability
diarylamino groups
accepting dimesitylboryl
>’- di
99 ).
51 ).
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.
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). 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.
2026-09-30T00:00:00Z
Text
Journal contribution
10.1021/acs.joc.6c00979.s001
https://figshare.com/articles/journal_contribution/Dual-State_Fluorescence_with_Efficiency_Close_to_Unity_from_D_-A-Type_Triarylborane-Based_Naphthalenes/34031227
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