This journal is © The Royal Society of Chemistry and the Chinese Chemical Society 2018 Mater. Chem. Front., 2018, 2, 1595--1608 | 1595
Cite this: Mater. Chem. Front.,
2018, 2, 1595
Recent progress in the mechanofluorochromism
of distyrylanthracene derivatives with
aggregation-induced emission
Juan Zhao, Zhihe Chi, Zhiyong Yang,* Zhu Mao, Yi Zhang, * Eethamukkala Ubba
and Zhenguo Chi *
Mechanofluorochromic (MFC) luminogens, as a group of evidence-based, practical smart materials, have
established immense interest with respect to mechanical stimuli, due to their promising applications in
various fields like mechanosensors, safety papers, and optical storage. However, MFC luminogens were
rare earlier than 2010. After the discovery that MFC is an essential unique feature of aggregation-induced
emission (AIE)-active molecules in 2011, researchers are encouraged to pay more attentions toward MCF
luminogens, in which field the investigations are hastened steadily and focused distinctly. As one of the
most vital AIE cores, distyrylanthracene (DSA) has been extensively used to assemble MFC motifs. As part
of the interest in MFC luminogens, this contemporary overview is targeted on recent advances in the
mechanofluorochromism of DSA derivatives with AIE properties and mechanistic study, which encourages
more researchers to dedicate themselves to this interesting exploration discipline.
1. Introduction
Mechanofluorochromic (MFC) luminogens are a class of smart
fluorescent molecules which can respond to external forces
including mechanical stimuli such as pressing, grinding,
crushing, or rubbing with alteration of the emission colors or
strengths, and have attracted considerable attention given their
promising applications in mechano-sensors, security papers,
and optical storage.
1–3
The emission of MFC luminogens can be
altered through changes in the molecular structure or aggregate
morphology. Although the first one is a general way to tune the
emission of a luminogen, limited examples of MFC luminogens
have been reported based on this mechanism due to their
incomplete and irreversible chemical reactions in the solid state.
Even though each system has its own characteristics, the MFC
luminescence of most reported luminogens has been achieved
during modulation in their morphology by mechanical stimuli.
4
However, prior to this essential discovery that mechanofluoro-
chromism is one of the common and unique properties for most
aggregation-induced emission (AIE) luminogens,
5
MFC lumino-
gens that are dependent on changes in their physical molecular
packing modes were very rare. There are two noticeable reasons:
6
firstly, there is a shortage of clear design strategies for their
syntheses; secondly, the emission of many luminogens is totally
or partially quenched when aggregates are formed due to the
aggregation-caused quenching (ACQ) effect.
In 2001, Tang et al.
7
suggested a few AIE molecules that emit
more efficiently in the aggregated state than in the dissolved
form, leading to key examples of anti-ACQ luminogens. Since
then, many AIE references such as triphenylethylene, tetraphenyl-
ethylene, silole, cyano distyrylbenzene and distyrylanthracene
have been used for the development of AIE molecules.
8–13
AIE
luminogens have become one of the hottest research topics due
to their potential applications in diverse fields, such as organic
light-emitting devices (OLEDs) and chemo-sensors.
14
In fact, the
development of AIE has surmounted the two aforementioned
problems. Recently, a number of AIE luminogens displaying
MFC properties have been discovered. For this reason, nowa-
days the use of AIE moieties provides an important strategy to
construct new compounds and also various mechano-responsive
AIE luminogens.
During the investigation of AIE, Tang and co-workers found
that several AIE luminogens can switch their emission between
bright and dark when crystalline and amorphous states are
interconverted.
15–17
The first reported investigation regarding
the mechano-responsive luminescence of an AIE molecule
18
attempted to prove the AIE mechanism, which was the restriction
of intramolecular rotations, by applying hydrostatic pressure to an
amorphous film of silole. It was found that the photoluminescence
(PL) emission intensity was enhanced by 9% when the pressure
PCFM Lab, GD HPPC Lab, Guangdong Engineering Technology Research Center for
High-performance Organic and Polymer Photoelectric Functional Films,
State Key Laboratory of Optoelectronic Material and Technologies,
School of Chemistry, Sun Yat-sen University, Guangzhou 510275, P. R. China.
E-mail: chizhg@mail.sysu.edu.cn, ceszy@mail.sysu.edu.cn,
yangzhy29@mail.sysu.edu.cn
Received 26th March 2018,
Accepted 20th May 2018
DOI: 10.1039/c8qm00130h
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