Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(14), P. 9575 - 9582
Published: March 27, 2024
Diarylethenes
belong
to
the
most
eminent
photoswitches
and
have
been
studied
for
many
decades.
They
are
found
in
virtually
every
field
of
application
become
highly
valuable
molecular
tools
instilling
light-responsiveness
into
materials,
catalysts,
biological
systems,
or
pharmacology.
In
this
work,
we
present
a
novel
distinct
type
pyrimidine-based
aza-diarylethene,
which
undergoes
unusual
zwitterion-forming
photoreaction.
During
fully
reversible
process,
CN
double
bond
is
established
under
concomitant
aromatization
thiophene-ring
opening.
The
metastable
zwitterion
thus
possesses
positively
charged
extended
aromatic
structure
an
independent
conjugated
thiolate
function.
It
can
further
photoisomerize
between
more
stable
Z
less
E
isomer,
resulting
effective
four-state
photoswitching.
Unusual
diarylethenes,
isomers
show
negative
solvatochromism
red-shifted
absorption
apolar
solvents.
With
behavior,
aza-diarylethenes
effectively
bridge
properties
merocyanines
diarylethenes.
Thermal
stability
zwitterions
be
modulated
from
very
labile
behavior
response
pH,
again
manner.
Pyrimidine-based
aza-diarylethene
establishes
unique
photoreaction
mechanism
allowing
control
charge
separation,
thermal
stability,
color
generation
different
way
than
hitherto
possible.
Chemical Reviews,
Journal Year:
2019,
Volume and Issue:
120(1), P. 310 - 433
Published: Dec. 23, 2019
Precise
control
over
molecular
movement
is
of
fundamental
and
practical
importance
in
physics,
biology,
chemistry.
At
nanoscale,
the
peculiar
functioning
principles
synthesis
individual
actuators
machines
has
been
subject
intense
investigations
debates
past
60
years.
In
this
review,
we
focus
on
design
collective
motions
that
are
achieved
by
integrating,
space
time,
several
or
many
these
mechanical
units
together.
particular,
provide
an
in-depth
look
at
intermolecular
couplings
used
to
physically
connect
a
number
artificial
mechanically
active
such
as
photochromic
switches,
nanomachines
based
bonds,
rotors,
light-powered
rotary
motors.
We
highlight
various
can
lead
their
motion
length
scales.
also
emphasize
how
synchronized,
desynchronized,
behavior
emerging
functional
properties
implementation
into
new
devices
materials.
Advanced Materials,
Journal Year:
2019,
Volume and Issue:
32(3)
Published: Feb. 18, 2019
Cyclodextrins
(CDs),
which
are
a
class
of
cyclic
oligosaccharides
extracted
from
the
enzymatic
degradation
starch,
often
utilized
in
molecular
recognition
and
assembly
constructs,
primarily
via
host-guest
interactions
water.
In
this
review,
recent
progress
CD-based
supramolecular
nanoassemblies
that
sensitive
to
chemical,
biological,
physical
stimuli
is
updated
reviewed,
intriguing
examples
biological
functions
these
presented,
including
pH-
redox-responsive
drug
gene
delivery,
enzyme-activated
specific
cargo
release,
photoswitchable
morphological
interconversion,
microtubular
aggregation,
cell-cell
communication,
as
well
geomagnetism-controlled
nanosystem
for
suppression
tumor
invasion
metastasis.
Moreover,
future
perspectives
challenges
fabrication
intelligent
biofunctional
materials
also
discussed
at
end
expected
promote
translational
development
nanomaterials
biomedical
field.
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
58(50), P. 18025 - 18031
Published: Oct. 4, 2019
Stimuli-responsive
photoluminescent
materials
have
attracted
considerable
attention
owing
to
their
potential
applications
in
security
protection
because
the
information
recorded
directly
with
static
luminescent
outputs
are
usually
visible
under
either
ambient
or
UV
light.
Herein,
we
realize
reversible
anticounterfeiting
by
loading
a
photoswitchable
diarylethene
derivative
into
lanthanide
metal-organic
framework
(MOF).
Light
triggers
open-
and
closed-form
isomerization
of
unit,
which
respectively
regulates
inactivation
activation
photochromic
FRET
process
between
acceptor
donor,
resulting
luminescence
on-off
switching
emitting
center
MOF
host.
This
photoresponsive
host-guest
system
allows
for
multiple
pattern
visible/invisible
transformation
simply
alternating
exposure
Chemical Science,
Journal Year:
2020,
Volume and Issue:
11(43), P. 11672 - 11691
Published: Jan. 1, 2020
This
perspective
article
explores
the
current
state
of
light-controlled
molecular
tools
for
medical
therapy
and
imaging
offers
an
outlook
on
clinical
application
scenarios
optimisation
strategies.
Advanced Functional Materials,
Journal Year:
2020,
Volume and Issue:
31(7)
Published: Nov. 3, 2020
Abstract
Fluorescent
photochromic
molecules
that
exhibit
distinct
light‐triggered
changes
in
their
emission
colors
are
highly
desirable
for
the
fabrication
of
smart
soft
materials
and
advanced
photonic
devices.
α‐Cyanodiarylethenes,
is,
α‐cyano‐functionalized
diarylethenes,
as
alternative
“non‐azo”
Z/E
molecular
switches,
popular
choices
due
to
unique
characteristics
such
aggregation‐induced
or
aggregation‐induced‐enhanced
behavior
self‐assembled
states,
visible
fluorescence
during
photoisomerization.
In
recent
years,
development
fluorescent
α‐cyanodiarylethene‐based
compounds
including
α‐cyanostilbenes,
dicyanodistyrylbenzenes,
diaryldicyanoethenes,
has
mainly
focused
on
design,
photochemical
photophysical
solution,
matter
technologies.
this
review,
significant
achievements
light‐responsive
systems
based
photoisomerization
α‐cyanodiarylethene
switches
span
range
from
liquid
crystals
gels
finally
nanostructures,
highlighted.
The
constructed
find
use
a
plethora
areas,
display,
sensing,
encrypting,
actuating,
biomedical
imaging
applications,
among
others.
review
concludes
with
brief
perspective
some
major
challenges
opportunities
future
materials.
Journal of the American Chemical Society,
Journal Year:
2018,
Volume and Issue:
140(50), P. 17691 - 17701
Published: Nov. 19, 2018
Multi-triggered
DNA/bipyridinium
dithienylethene
(DTE)
hybrid
carboxymethyl
cellulose
(CMC)-based
hydrogels
are
introduced.
DTE
exhibits
cyclic
and
reversible
photoisomerization
properties,
switching
between
the
closed
state
(DTEc),
electron
acceptor,
open
isomer
(DTEo)
that
lacks
acceptor
properties.
One
system
introduces
a
dual
stimuli-responsive
hydrogel
containing
CMC
chains
modified
with
donor
dopamine
sites
self-complementary
nucleic
acids.
In
presence
of
DTEc
scaffold,
stiff
is
formed,
cooperatively
stabilized
by
dopamine/DTEc
donor–acceptor
interactions
duplex
The
formation
dissociation
supramolecular
interactions,
through
light-induced
DTE,
or
via
oxidation
subsequent
reduction
sites,
leads
to
switchable
stiffness.
Another
triggered
one
three
alternative
signals.
stiff,
multi-triggered
consists
cross-linked
K+-stabilized
G-quadruplexes.
G-quadruplexes
reversibly
separated
in
18-crown-6
ether
reformed
upon
addition
K+.
undergoes
transitions
high-stiffness
low-stiffness
states
light,
redox
agents,
K+/crown
ether.
donor–acceptor/G-quadruplex
shows
shape-memory
self-healing
features.
By
using
different
triggers
two
memory-codes,
e.g.,
G-quadruplexes,
guided
function
matrices
demonstrated.
Journal of the American Chemical Society,
Journal Year:
2019,
Volume and Issue:
141(5), P. 2097 - 2103
Published: Jan. 8, 2019
Photochromic
[Pd2L4]
coordination
cages
based
on
dithienylethene
(DTE)
ligands
L
allow
triggering
guest
uptake
and
release
by
irradiation
with
light
of
different
wavelengths.
The
process
involves
four
consecutive
electrocyclic
reactions
to
convert
all
chromophores
between
their
open
closed
photoisomeric
forms.
So
far,
affinity
the
fully
switched
species
was
elucidated,
but
mechanistic
details
concerning
intermediate
steps
remained
elusive.
Now,
a
new
member
DTE
cage
family
allows
unprecedented
insight
into
interplay
photoisomerization
location
inside/outside
cavity.
Therefore,
intrinsic
chirality
backbones
used
as
reporter
for
monitoring
fate
chiral
guest.
In
its
"open"
form
(
o-L,
[Pd2(
o-L)4]
=
o-C),
C2-symmetric
chromophore
quickly
converts
energetically
degenerate
P
M
helical
conformations.
After
binding
homochiral
1
R-(
-)
or
S-(
+)
camphor
sulfonate
R-CSA
S-CSA),
guest-to-host
transfer
observed
via
circular
dichroism
(CD)
signal
cage-centered
absorption.
Irradiating
R/S-CSA@
o-C
host-guest
complexes
at
313
nm
produced
configurationally
stable
"closed"
photoisomers,
thus
locking
induced
an
enantiomeric
excess
close
25%.
This
value
(corresponding
induction
one
out
ligands),
together
DOSY
NMR,
ion
mobility
mass
spectrometry,
X-ray
structure
results,
shows
that
closure
first
photoswitch
is
sufficient
expel
from
Advanced Materials,
Journal Year:
2021,
Volume and Issue:
34(16)
Published: Dec. 6, 2021
Diarylethene
(DAE)
photoswitch
is
a
new
and
promising
family
of
photochromic
molecules
has
shown
superior
performance
as
smart
trigger
in
stimulus-responsive
materials.
During
the
past
few
decades,
DAE
achieved
leap
from
simple
to
functional
developed
toward
validity
universal
switching
building
block.
In
recent
years,
introduction
into
an
assembly
system
been
attractive
strategy
that
enables
behavior
blocks
be
manifested
at
level
entire
system,
beyond
unit
itself.
This
assembly-based
will
bring
many
unexpected
results
promote
design
manufacture
generation
advanced
Here,
advances
fabrication
diarylethene
materials
science,
chemistry,
biomedicine
are
reviewed.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(31)
Published: May 7, 2022
Abstract
Light
offers
unique
opportunities
for
controlling
the
activity
of
materials
and
biosystems
with
high
spatiotemporal
resolution.
Molecular
photoswitches
are
chromophores
that
undergo
reversible
isomerization
between
different
states
upon
irradiation
light,
allowing
a
convenient
means
to
control
their
influence
over
system
interest.
However,
significant
limitation
classical
is
requirement
initiate
switching
in
one
or
both
directions
using
deleterious
UV
light
poor
tissue
penetration.
Red‐shifted
hence
demand
have
attracted
keen
recent
research
In
this
Review,
we
highlight
progress
towards
development
visible‐
NIR‐activated
characterized
by
distinct
photochromic
reaction
mechanisms.
We
hope
inspire
further
endeavors
field,
full
potential
these
tools
biotechnology
chemistry
applications
be
realized.