Thiophene-containing
heteroarenes
are
one
of
the
most
well-known
classes
π-conjugated
building
blocks
for
photoactive
molecules.
Isomeric
naphthodithiophenes
(NDTs)
at
forefront
this
research
area
due
to
their
straightforward
synthesis
and
derivatization.
Notably,
NDT
geometries
that
bent
–
such
as
naphtho[2,1-b:3,4-b’]dithiophene
(α-NDT)
naphtho[1,2-b:4,3-b’]dithiophene
(β
-NDT)
seldom
employed
small
This
report
investigates
how
remote
substituents
impact
photophysical
properties
isomeric
α-
β-NDTs.
The
orientation
thiophene
units
plays
a
critical
role
in
emission:
α(OHex)R2
series
conjugation
from
end-caps
core
is
apparent,
while
β(Oi-Pent)R2
minimal
change
observed
unless
strong
electron
acceptors,
β(Oi-Pent)(PhCF3)2,
employed.
push-pull
Acceptor–Donor–Acceptor
(A–D–A)
fluorophore
exhibits
positive
fluorosolvatochromism
correlates
with
increasing
solvent
polarity
parameter,
ET(30).
In
total,
these
results
highlight
able
modulate
emission
NDTs.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(4), P. 781 - 785
Published: Jan. 19, 2024
A
pair
of
novel
chiral
1-phenylethylamine-modified
twistarenes
(4
and
11;
compound
4
=
9,14-di-tert-butyl-7,16-diphenyl-2-(1-phenylethyl)-1H-benzo[8',9']triphenyleno[2',3':6,7]fluoreno[2,1,9-def]isoquinoline-1,3(2H)-dione)
have
been
synthesized
characterized,
how
the
solvent
component
affects
chirality
transfer
their
self-assembled
processes
is
investigated
in
mixtures
with
THF
H2O.
The
ordered
assembly
11
exhibits
circular
dichroism
response.
In
addition,
both
11a
11b
display
positive
photoconducting
behavior.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(19), P. 5638 - 5669
Published: Jan. 1, 2024
This
review
covers
recent
advances
in
post-functionalization
of
twistacenes
to
realize
polyacenes,
chiral
nanographenes
and
their
semiconductor
properties,
emphasizing
a
promising
future
for
constructing
nanotubes.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(33)
Published: July 5, 2023
Abstract
The
synthesis
of
three
penta‐
and
hexahelicenes
containing
two
terminal
thiophene
units
is
described.
syntheses
pentahelicenes
consist
1,4‐bisalkynylation
a
benzene
precursor
double
Suzuki
coupling
in
2,3‐position
to
introduce
units.
ortho
,
’
fusion
yielding
the
final
products
was
achieved
with
Fürstner's
protocol
using
platinum(II)
chloride
or
JohnPhos‐complexed
gold(I)
as
catalysts.
A
similar
approach
started
naphthalene
derivative,
where
2,7‐bisalkynylation
subsequent
thiophene‐2‐boronic
acid
at
1,8‐position
furnished
precursors,
which
respective
or,
favourably,
indium(III)
chloride.
UV/Vis
spectra
cyclic
voltammograms
were
recorded
for
all
helicenes
HOMO/LUMO
gaps
calculated
DFT
methods.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14550 - 14558
Published: Oct. 9, 2023
Two
pairs
of
isomers
heptagon-embedded
helical
arenes
(3/6
and
10/13)
have
been
strategically
prepared,
where
the
molecular
structures
3
13
identified
through
single
crystal
X-ray
diffraction
analysis.
The
effect
heptagon
unit
on
physical
properties
3,
6,
10,
is
investigated
in
a
comparative
manner,
results
indicate
that
optical
enantiomers
obtained
from
HPLC
exhibit
promising
chiroptical
properties.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
30(3)
Published: Oct. 23, 2023
Two
new
pentagon-embedded
carbo[11]helicenes
have
been
designed
and
synthesized
in
a
three-step
process,
which
are
the
first
example
of
through
post-functionalization
twistacene.
TD-DFT
analyses
indicate
that
both
them
possess
high
enantiomerization
barriers
42.29
kcal/mol
40.76
kcal/mol,
respectively.
They
emit
strong
red
fluorescence
can
be
chemically
oxidized
into
stable
cationic
radicals
upon
addition
AgSbF
Nanoscale,
Journal Year:
2024,
Volume and Issue:
16(10), P. 5395 - 5400
Published: Jan. 1, 2024
Two
novel
coumarin-embedded
π-extended
[5]helicene
derivatives
(3a
and
6a)
have
been
strategically
synthesized
characterized,
the
structure
of
3a
was
determined
via
single
crystal
X-ray
analysis.
RSC Advances,
Journal Year:
2024,
Volume and Issue:
14(35), P. 25120 - 25129
Published: Jan. 1, 2024
Thiophene-containing
heteroarenes
are
one
of
the
most
well-known
classes
π-conjugated
building
blocks
for
photoactive
molecules.
Isomeric
naphthodithiophenes
(NDTs)
at
forefront
this
research
area
due
to
their
straightforward
synthesis
and
derivatization.
Notably,
NDT
geometries
that
bent
-
such
as
naphtho[2,1-
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(34), P. 7088 - 7093
Published: Aug. 15, 2024
A
family
of
chiral
nanographenes
bearing
[6]helicene
units
has
been
synthesized
via
the
classical
Scholl
reaction.
Inserting
unit
into
parent
nanographene
skeleton
can
result
in
different
structural
topologies
and
optoelectric
properties.
Moreover,
isolated
enantiomers
exhibit
attractive
chiroptical
