Bulletin of the Chemical Society of Japan,
Год журнала:
2018,
Номер
92(1), С. 152 - 161
Опубликована: Окт. 4, 2018
Abstract
In
this
paper,
we
summarize
recent
developments
made
by
our
group
in
direct
arylation
polycondensation.
The
method
under
optimal
conditions
affords
a
high-molecular-weight
polymer
with
high
purity
through
simple
purification
process.
high-quality
polymers
have
been
used
as
active
materials
for
optoelectronic
applications
and
show
equivalent
or
superior
performance
to
the
same
prepared
conventional
methods.
development
of
facile
synthetic
protocols
could
increase
their
practical
applications.
Recent
C-H/C-H
coupling
polycondensation
are
also
described.
Macromolecules,
Год журнала:
2017,
Номер
50(18), С. 7080 - 7090
Опубликована: Сен. 15, 2017
Diketopyrrolopyrrole
(DPP)
derivatives
are
among
the
most
efficient
materials
studied
for
both
polymer
solar
cells
(PSCs)
and
organic
field-effect
transistors
(OFETs)
applications.
We
report
here
synthesis
of
new
fluorinated
dithienyldiketopyrrolopyrrole
(fDT-DPP)
monomers
suitable
direct
heteroarylation
polymerization.
fDT-DPP
copolymers
were
then
prepared
to
probe
effect
fluorination.
It
was
found
that
they
feature
deeper
HOMO
energy
levels
smaller
bandgaps
than
their
non-fluorinated
analogues.
Moreover,
some
show
ambipolar
behavior
when
tested
in
OFETs.
For
example,
P2
shows
hole
mobility
up
0.8
cm2
V–1
s–1
electron
0.5
s–1.
Inverted
PSCs
with
power
conversion
efficiency
(PCE)
7.5%
also
obtained
P5.
These
results
reported
(OFETs
PSCs)
confirm
fluorination
dithienyl-DPP
moieties
improves
performance
electronics
devices.
This
study
is
evidencing
strength
polymerization
as
a
class
conjugated
polymers.
Chemistry of Materials,
Год журнала:
2018,
Номер
30(15), С. 5353 - 5361
Опубликована: Июль 9, 2018
A
high
molecular
weight
alternating
naphthalene
diimide–bithiophene
copolymer
(poly{[N,N′-bis(2-octyldodecyl)-naphthalene-1,4,5,8-bis(dicarboximide)-2,6-diyl]-alt-5,5′-(2,2′-bithiophene)}
(PNDIOD-T2))
has
been
prepared
by
direct
(hetero)arylation
polymerization
(DHAP).
Its
structure
and
properties
were
investigated
in
comparison
with
the
Stille-prepared
commercial
analog,
N2200.
It
was
found
that
new
DHAP-derived
PNDIOD-T2
known
N2200
have
similar
optical
absorption
spectra
HOMO/LUMO
energy
levels
but
slightly
different
1H
NMR
spectra.
Inverted
all-polymer
solar
cells
using
as
acceptor
PCE12
or
PCE10
donor
polymer
showed
superior
performances
compared
to
devices.
All-polymer
7.3%
efficiency
could
be
achieved
blends
without
use
of
a
processing
additive.
These
results
demonstrate
low-cost
eco-friendly
DHAP-based
n-type
semiconducting
polymers
are
promising
for
developing
performance
cells.
ACS Macro Letters,
Год журнала:
2017,
Номер
7(1), С. 90 - 94
Опубликована: Дек. 26, 2017
Polycondensation
via
Pd-catalyzed
cross-dehydrogenative-coupling
reaction
of
2,2',3,3',5,5',6,6'-octafluorobiphenyl
with
thiophene
analogues
was
studied.
The
synthetic
protocol,
in
which
employment
prefunctionalized
starting
monomers
fully
avoided,
allowed
straightforward
access
to
an
alternating
π-conjugated
polymer.
addition
K2CO3
the
catalytic
system
promotes
cross-coupling
and
suppresses
undesired
homocoupling
reaction,
producing
corresponding
donor-acceptor
type
polymers
minor
defects.
also
proceeded
using
O2
as
terminal
oxidant,
resulting
lower
loading
Ag
oxidant.
obtained
polymer
evaluated
emitting
material
for
organic
light-emitting
diode.
Macromolecules,
Год журнала:
2021,
Номер
54(12), С. 5464 - 5472
Опубликована: Июнь 10, 2021
The
synthesis
of
water-processable
self-doped
polymers
has
been
achieved
by
direct
(hetero)arylation
polymerization
(DHAP)
using
water
as
a
cosolvent.
introduction
counterion
covalently
attached
to
the
backbone
enhanced
their
solubility
and
stability
solutions.
Those
have
shown
air-stable
electrical
conductivities
up
50
S
cm–1
without
use
any
post-treatment.
good
processability
these
conducting
is
promising
for
printed
electronics
in
wide
range
applications.
The
environmental
impact
of
solution
processed
organic
solar
cells
(OSCs)
can
be
mitigated
by
introducing
so‐called
green
solvents
during
the
fabrication
processes.
However,
effects
such
on
molecular‐level
structures
and
optoelectronic
properties
lack
in‐depth
characterization.
Here,
insights
into
structure–processing–property
correlation
a
PPDT2FBT:PC
61
BM
bulk‐heterojunction
(BHJ)
system
from
solvent,
ortho
‐xylene
(
o
‐XY),
is
investigated
in
comparison
with
same
blend
traditional
halogenated
chlorobenzene
(CB).
BHJ
blends
are
characterized
various
techniques
probing
at
difference
length
scales,
an
increased
donor:acceptor
(D:A)
interfacial
area
as
well
well‐mixed
features
bulk
morphologies
active
layer
observed
for
‐XY
blend.
Furthermore,
differences
D–A
intermolecular
interactions
interfaces
CB
cast
films
elucidated
2‐dimensional
solid‐state
nuclear
magnetic
resonance
(ssNMR)
measurements
analysis.
These
results
consistent
device
properties,
suggesting
that
green‐solvent‐processed
devices
have
longer
charge
carrier
lifetimes
faster
extraction.
optimized
achieve
noteworthy
higher
power
conversion
efficiency
(PCE)
owing
to
short‐circuit
current
density
fill
factor.
ACS Materials Letters,
Год журнала:
2021,
Номер
3(10), С. 1503 - 1512
Опубликована: Сен. 16, 2021
The
development,
optimization,
and
assessment
of
new
methods
for
the
preparation
conjugated
materials
is
key
to
continued
progress
organic
electronics.
Direct
C–H
activation
have
emerged
developed
over
last
10
years
become
an
invaluable
synthetic
tool
polymers
both
redox-active
solid-state
applications.
Here,
we
evaluate
direct
(hetero)arylation
polymerization
(DHAP)
synthesis
indaceno[1,2-b:5,6-b′]dithiophene-based
polymers.
We
demonstrate,
using
a
range
techniques,
including
visualization
individual
polymer
chains
via
high-resolution
scanning
tunneling
microscopy,
that
DHAP
can
produce
with
high
degree
regularity
purity
subsequently
perform
in
thin-film
transistors
comparably
those
made
by
other
cross-coupling
polymerizations
require
increased
complexity.
Ultimately,
this
work
results
improved
atom
economy
reducing
number
steps
access
high-performance
molecular
polymeric
materials.
Journal of Polymer Science,
Год журнала:
2021,
Номер
60(3), С. 393 - 428
Опубликована: Сен. 15, 2021
Abstract
In
the
past
decade,
direct
arylation
polymerization
(DArP)
has
rapidly
developed
as
a
sustainable
synthetic
protocol
for
cost‐effective,
atom‐economical
preparation
of
conjugated
polymers.
By
circumventing
monomer
functionalization
with
toxic
transmetallating
reagents
such
organostannane
and
organoboron
required
Stille‐Migita
Suzuki‐Miyaura
methods,
DArP
proceeds
through
metal‐catalyzed
CH
activation
pathway
high‐performance
polymer
materials.
This
review
evaluates
development
several
classes
efficient
catalysts/catalytic
systems
from
small‐molecule
studies
to
polymerizations,
including
mechanisms
involved
in
these
transformations
how
they
inspire
catalyst
design
defect‐free
synthesis.
Recent
advances
developing
more
first‐row
transition
metal
catalysts
are
also
highlighted,
fundamental
understanding
should
motivate
pursuit
next
generation
catalytic
enable
effective
environmentally
friendly
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(7), С. 4208 - 4220
Опубликована: Фев. 10, 2023
Fluorescent
polyelectrolytes
have
attracted
enormous
attention
as
functional
polymer
materials.
In
contrast
with
the
widely
studied
conjugated
ionic
groups
in
side
chains,
fluorescent
main-chain
charged
(MCCPs)
rarely
been
explored
due
to
large
synthetic
difficulty.
Herein,
we
develop
a
facile
and
atom-economical
