The
level
of
fluoride
ions
(F
-)
in
the
human
body
is
closely
related
to
various
pathological
and
physiological
states,
rapid
detection
F-
important
for
studying
processes
early
diagnosis
diseases.
In
this
study,
detailed
sensing
mechanism
a
novel
high-efficiency
probe
(PBT)
based
on
2-(2'-hydroxyphenyl)-benzothiazole
derivatives
towards
has
been
fully
investigated
density
functional
theory
(DFT)
time-dependent
(TDDFT)
methods.
attacking
O-P
bond
PBT
cleavage
dimethylphosphinothionyl
group,
potential
products
were
evaluated
by
Gibbs
free
energy
spectroscopic
analyses,
which
ultimately
identified
product
as
HBT-Enol1
with
an
intramolecular
hydrogen
bond.
Bond
parameters,
infrared
vibrational
spectroscopy
charge
analysis
indicate
that
enhanced
at
excited
state
(S1),
favoring
proton
transfer
(ESIPT).
mild
barrier
further
evidences
occurrence
ESIPT.
Combined
Frontier-molecular-orbital
(FMO)-analysis,
fluorescence
quenching
was
attributed
photoinduced
electron
(PET)
turn-on
ESIPT
process
HBT-Enol1.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(7), P. 1541 - 1541
Published: March 29, 2024
The
level
of
fluoride
ions
(F−)
in
the
human
body
is
closely
related
to
various
pathological
and
physiological
states,
rapid
detection
F−
important
for
studying
processes
early
diagnosis
diseases.
In
this
study,
detailed
sensing
mechanism
a
novel
high-efficiency
probe
(PBT)
based
on
2-(2′-hydroxyphenyl)-benzothiazole
derivatives
towards
has
been
fully
investigated
density
functional
theory
(DFT)
time-dependent
(TDDFT)
methods.
attacks
O-P
bond
PBT
cleavage
dimethylphosphinothionyl
group,
potential
products
were
evaluated
by
Gibbs
free
energy
spectroscopic
analyses,
which
ultimately
identified
product
as
HBT-Enol1
with
an
intramolecular
hydrogen
bond.
Bond
parameters,
infrared
vibrational
spectroscopy
charge
analysis
indicate
that
enhanced
at
excited
state
(S1),
favoring
proton
transfer
(ESIPT).
mild
barrier
further
evidences
occurrence
ESIPT.
Combined
frontier
molecular
orbital
(FMO)
analysis,
fluorescence
quenching
was
attributed
photoinduced
electron
(PET)
turn-on
ESIPT
process
HBT-Enol1.
ChemistrySelect,
Journal Year:
2023,
Volume and Issue:
8(25)
Published: July 3, 2023
Abstract
Inspired
by
the
excellent
photochemical
properties
of
2‐(2′‐hydroxyphenyl)benzazole
and
its
derivatives,
in
this
work,
novel
2‐bis(benzothia‐zolyl)naphthalene‐diol
(2‐BBTND)
fluorophore
is
explored
about
photo‐induced
behaviors.
The
intramolecular
double
hydrogen
bonding
interaction
excited
state
proton
transfer
(ESDPT)
behavior
2‐BBTND
are
investigated
combination
with
different
polar
solvent
environments.
From
structural
changes
charge
recombination
induced
photoexcitation,
we
can
affirm
that
strong
environment
promotes
dynamical
reaction
for
compound.
By
constructing
potential
energy
surfaces
(PESs)
S
0
1
states,
clarify
should
undergo
stepwise
ESDPT
after
photoexcitation.
Combined
size
barriers
along
paths
solvents,
finally
propose
a
new
solvent‐polarity‐dependent
fluorophore.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 25, 2024
A
novel
fluorophore
2-(2′-hydroxy-5′-benzaldehyde
phenyl)
benzothiazole
(HBBT)
with
excited
state
intramolecular
proton
transfer
(ESIPT)
characteristics,
showing
good
selectivity
for
Cu+/Cu2+
ions
had
been
synthesized
experimentally
(Molecules
2022,
27,
7678).
However,
its
ESIPT
mechanism
and
fluorescent
performance
related
to
atomic
substituents
have
not
investigated
systematically.
In
this
work,
two
HBBT
derivatives,
phenyl)benzoimidazole
(HBBI)
phenyl)benzopyrrole
(HBBP),
were
obtained
by
respectively
using
−NH
−CH2
groups
in
place
of
the
sulfur
atom
thiazole
ring.
The
absorption/emission
spectra
ring
aromaticity
as
well
processes
derivatives
studied
density
functional
theory
(DFT)
time-dependent
DFT
(TD-DFT).
simulated
absorption
fluorescence
wavelengths
agreed
corresponding
values
experiment.
According
analyses
geometry
structures,
electron
densities,
infrared
vibration
frequencies,
hydrogen
bond
becomes
stronger
upon
light
excitation.
frontier
molecular
orbitals
analyzed
via
establishing
potential
energy
curves,
behavior
was
described
deeply.
Obviously,
NH–substitution
makes
4
more
aromatic,
while
CH2–substitution
changes
from
aromatic
antiaromatic.
process
helps
alleviate
antiaromaticity.
greater
antiaromaticity
S1
normal
form,
higher
barrier
ESIPT.
International Journal of Molecular Sciences,
Journal Year:
2023,
Volume and Issue:
24(18), P. 13899 - 13899
Published: Sept. 9, 2023
The
mechanism
of
fluorescence
detection
diethyl
chlorophosphate
(DCP)
based
on
2-substituted
benzothiazole
(BZ-DAM)
was
studied
by
a
theoretical
calculation
method.
It
should
not
be
ignored
that
both
the
BZ-DAM
and
product
BZ-CHO
have
two
excited-state
intramolecular
proton
transfer
(ESIPT)
channels.
Density
functional
theory
(DFT)
time-dependent
DFT
(TDDFT)
were
used
to
study
photophysical
compounds
in
channels
(acetonitrile)
ACN
solvent,
temperature
dependence
given.
Channel
1
is
more
likely
exist
at
low
temperatures
channel
2
high
temperatures.
By
analysis
constructed
potential
energy
curve,
hydrogen
bond
electron-hole
analysis,
we
confirmed
molecules
undergo
ESIPT
charge
(ICT)
processes
twisted
(TICT)
coupling
2.
formation
led
significant
blue-shift
phenomenon
inhibited
ICT
process,
which
could
as
probe
for
detection.
We
sincerely
hope
this
work
will
only
help
clarify
dynamics
behavior
but
also
provide
new
idea
designing
optimizing
chemical
dosimeter.
