Trifluoroacetyl‐Substituted D–π–A Fluorophores: Design Strategies for Strong Solvatochromism and Giga Stokes Shifts
Chemistry - An Asian Journal,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 30, 2025
Solvatochromic
fluorophores,
widely
employed
in
various
analytical
applications
such
as
environmentally
responsive
dyes,
typically
feature
a
donor-π-acceptor
(D-π-A)
structure.
Most
recently,
Klymchenko
and
we
independently
designed
D-π-A
fluorophores
with
strong
acceptor,
trifluoroacetyl
group,
to
achieve
fluorescent
solvatochromism
reported
its
application
membrane
analysis
(Klymchenko
et
al.
Anal.
Chem.
2024,
96,
13242)
molecular
thermometer
(Konishi
J.
Am.
Soc.
2025,
147,
9953),
respectively.
However,
these
reports
have
only
considered
few
π-electron
donors
including
dialkylamines.
There
is
not
enough
scope
for
solvatochromic
that
take
advantage
of
the
properties
group.
In
this
study,
systematically
investigated
π-conjugated
aromatic
skeleton
groups.
The
relationship
between
dye
structure
absorption,
fluorescence,
quantum
yield
were
clarified,
design
strategy
exhibit
desired
was
established.
Moreover,
fluorescence
quenching
can
occur
depending
on
solvent
selection
or
study
provides
insightful
trifluoroacetyl-based
strategy,
emphasizing
their
prospective
but
underused
acceptor
units
next
fluorophore
development.
Language: Английский
Triphenylamine[3]arenes: Streamlining Synthesis of a Versatile Macrocyclic Platform for Supramolecular Architectures and Functionalities
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: May 21, 2024
Triphenylamine[3]arenes
(TPA[3]s),
featuring
[1
Language: Английский
Triphenylamine[3]arenes: Streamlining Synthesis of a Versatile Macrocyclic Platform for Supramolecular Architectures and Functionalities
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
unknown
Published: May 21, 2024
Abstract
Triphenylamine[3]arenes
(TPA[3]s),
featuring
[1
6
]paracyclophane
backbone
with
alternating
carbon
and
nitrogen
bridging
atoms,
were
synthesized
through
a
BF
3
⋅
Et
2
O‐catalyzed
cyclization
reaction
using
triphenylamine
derivatized
monomers
paraformaldehyde.
This
molecular
design
yielded
series
of
TPA[3]
macrocycles
high
efficiency,
their
facile
derivatizations
also
successfully
demonstrated.
On
account
the
strong
electron‐donating
properties
TPA
moieties,
these
TPA[3]s
exhibit
remarkable
delayed
fluorescence,
possess
significant
affinity
for
iodine.
Furthermore,
inherent
three‐fold
symmetry
rendered
as
novel
building
blocks
construction
extended
frameworks
cages.
advancement
expands
versatility
discrete
into
complex
architectures,
enhancing
applicability
across
broad
spectrum
applications.
Language: Английский