Angewandte Chemie,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 18, 2024
Abstract
The
synthesis
and
stabilization
of
heteroatom‐doped
nanocarbon
molecules,
such
as
carbazole‐containing
(super)helicenes,
present
significant
challenges
due
to
the
complexities
involved
in
maintaining
structural
integrity
electronic
functionality.
In
this
study,
we
successfully
synthesized
a
carbazole‐centered
expanded
tris‐hexabenzo[7]helicene
(
1
)
via
facile
FeCl
3
‐mediated
Scholl
coupling
reaction.
exhibits
both
chemical
chiral
stability
demonstrates
fluorescence
at
628
nm
with
quantum
yield
0.40.
Additionally,
enantiomers
display
pronounced
chiroptical
properties,
including
distinct
circular
dichroism
(CD)
signal
spanning
from
300
600
nm.
absorption
dissymmetry
factor
(|
g
abs
|)
is
determined
be
2.98×10
−3
,
while
circularly
polarized
luminescence
brightness
B
CPL
measured
32.50
M
−1
cm
.
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 7, 2025
Azuacenes,
defined
as
azulene
fused
with
acenes
in
a
6-7-5
ring
topology
and
spanning
lengths
from
3
to
6
rings,
have
been
synthesized
using
new
skeleton
editing
[3
+
2]
annulation
synthesis
protocol
distinction
regarding
the
procedures
obtain
6-5-7
isomers.
Comprehensive
studies
on
ground-state
excited-state
spectroscopy,
electrochemical
properties,
chemical
stability,
solid-state
structure
conducted
compare
these
azuacenes
acenes.
For
same
number
of
we
found
that
improve
stability
(i.e.,
smaller
diradical
character)
their
photophysical
properties
anti-Kasha
emissions
modulation
energy
strength
visible
bands)
but
they
reduce
transport
features
compared
those
Compared
azulene,
performance
terms
electrical
properties.
Overall,
fusion
known
polycyclic
compounds,
such
acene
produces
isomeric
hybrid
compounds
enhanced
Here,
resulting
turn
out
conserve
most
unique
two
building
blocks
associate
facility
π-delocalization
positive
charge
zwitterion
over
fragment.
For
more
than
a
century,
electrophilic
aromatic
substitution
reactions
have
been
central
to
the
construction
of
rich
variety
organic
molecules
that
are
useful
in
all
aspects
human
life.
Typically,
small
nuclei,
such
as
benzene,
provide
an
ideal
substrate.
An
increase
number
annulated
rings
enhances
potential
reactive
sites
and
frequently
results
complex
product
mixtures.
Thus,
nanographenes
with
relatively
large
system
seldom
selective
their
positions.
Moreover,
nanographene
substrates
scope
for
multiple
patterns
remain
rare.
Herein,
we
demonstrate
curved
based
on
corannulene-coronene
hybrid
structure
comprising
48
conjugated
sp
2-carbon
atoms
allows
direct
regioselective
edge
functionalization
through
bromination,
nitration,
formylation,
Friedel-Crafts
acylation
good
yields.
The
postsynthetically
installed
functional
groups
can
be
modified
versatile
chemistry
transformations,
including
(mechanochemical)
Suzuki-Miyaura,
Sonogashira-Hagihara,
Buchwald-Hartwig
amination
reactions.
Furthermore,
substitutions
carried
out
sequential
manner
yield
heterofunctional
structures.
edge-functionalization
strategy
enables
modular
access
nanostructures
appealing
properties,
strong
fluorescence
emission
visible
near-infrared
regions
(475-900
nm)
record
Stokes
shifts
(>300
nm),
at
exceptionally
carbon
footprint
(C48).
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(32), С. 22600 - 22611
Опубликована: Авг. 5, 2024
Atomically
precise
synthesis
of
three-dimensional
boron-nitrogen
(BN)-based
helical
structures
constitutes
an
undeveloped
field
with
challenges
in
synthetic
chemistry.
Herein,
we
synthesized
and
comprehensively
characterized
a
new
class
molecular
carbons,
named
benzo-extended
[n]heli(aminoborane)s
(
Chemical Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Axially
chiral
substrates
were
transformed
into
enantiomer-enriched
π-extended
helicenes
via
a
chiral-transfer-based
Scholl
reaction,
and
enantiomers
efficiently
separated
without
labor-intensive
high-performance
liquid
chromatography
(HPLC).
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 25, 2024
Comprehensive
Summary
As
a
class
of
organic
dyes,
boron‐containing
compounds
play
an
important
role
in
luminescent
materials.
They
have
attracted
considerable
attention
due
to
their
unique
photophysical
properties.
Chiral
systems
wide
range
practical
applications
biological
imaging,
optoelectronic
devices,
information
storage
and
3D
display.
Boron‐containing
chiral
materials
can
not
only
effectively
improve
the
properties
CPL
materials,
but
also
bring
system,
which
enables
them
be
used
as
favorable
emitting
for
expanded
applications.
Here,
we
review
research
progress
by
detailed
discuss
according
different
skeletons,
such
point
chirality,
1,1’‐binaphthyl,
[
n
]helicenes,
[2,2]paracyclophane
pillar[5]arenes.
We
believe
that
this
is
significance
development
Key
Scientists
The
studies
circularly
polarized
luminescence
(CPL)
based
on
small
molecules
advanced
significantly.
However,
gained
recent
years.
In
2019,
Zhao's
group
prepared
binaphthalene
derivative
modified
with
triarylborane,
representing
molecule
material
exhibit
characteristics
responsive
both
solvent
fluoride
ions.
2020,
Chen's
steric
effects
triarylborane
triphenylamine
prepare
planar
2021,
Wang's
developed
new
B,N‐embedded
double
hetero[7]helicenes
strong
chiroptical
responses
UV‐visible
region.
same
year,
He's
asymmetric
reactions
synthesize
boron‐based
point‐chirality
high
efficiency
enantioselectivity.
2023,
Ravat
synthesized
1,4‐B,N‐embedded
helicenes
exhibiting
narrow‐band
fluorescence
CPL.
During
period,
Matthias
Wagner
et
al
obtained
(BO)
2
‐doped
tetrathia[7]helicene
via
efficient
four‐step
synthesis,
Zheng
reported
nearly
pure
green
electroluminescent
device
(CP‐OLED).
2024,
hetero‐[9]helicenes
offering
pathway
towards
significantly
enhanced
helicene‐based
CPEL.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 18, 2024
The
synthesis
and
stabilization
of
heteroatom-doped
nanocarbon
molecules,
such
as
carbazole-containing
(super)helicenes,
present
significant
challenges
due
to
the
complexities
involved
in
maintaining
structural
integrity
electronic
functionality.
In
this
study,
we
successfully
synthesized
a
carbazole-centered
expanded
tris-hexabenzo[7]helicene
(1)
via
facile
FeCl
Advanced Optical Materials,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 16, 2024
Abstract
Thiahelicenes,
an
important
subclass
of
helicenes,
are
renowned
for
their
pronounced
chiroptical
properties,
particularly
circular
dichroism.
However,
the
exploration
circularly
polarized
luminescence
(CPL)
has
been
hindered
due
to
inherently
weak
fluorescence,
leaving
a
critical
gap
in
development
thiahelicenes
as
efficient
CPL
emitters.
To
address
this
limitation,
novel
strategy
enhancing
by
integrating
thiophene‐containing
units
with
highly
emissive
hexabenzoperylene
(HBP)
core
is
presented.
Two
isomeric
HBP‐cored
double
synthesized,
which
serve
proof
concept.
These
molecules
exhibit
exceptionally
high
fluorescence
quantum
yields
(
Φ
F
=
83%
and
91%),
surpassing
all
previously
reported
thiahelicenes.
Furthermore,
dissymmetry
factors
show
four‐fold
enhancement
compared
parent
HBP,
resulting
remarkable
brightness
up
84.9
M
−1
cm
.
findings
not
only
limitation
but
also
establish
new
pathway
developing
high‐performance
materials.
