1, 3-Indanedione functionalized fluorene luminophores: Negative solvatochromism, nanostructure-morphology determined AIE and mechanoresponsive luminescence turn-on

Article abstract of DOI:10.1016/j.dyepig.2018.03.059

Luminous efficiency in polar environment and aggregated state, as well as high-contrast luminescence on/off switching under external stimuli are significant issues to be addressed in developing functional fluorescent materials. Combining the advantages of solvatochromic effect in intramolecular charge transfer (ICT) compounds with their nanostructured morphological effects, we herein report a series of A–π–D–π–A fluorene derivatives, which simultaneously exhibit negative solvatochromism, aggregation-induced emission (AIE) and mechanoresponsive luminescence (MRL) turn-on. These molecules contain the same fluorene donor (D) and 1,3-indandione acceptor (A) but differ in alkyl substituents in the 9-position of the fluorene segment, including 9,9-dibutyl (b-DIPF), 9,9-dioctyl (o-DIPF) and 9,9-didodecyl (d-DIPF). The emission colors of these compounds were changed from blue to orange-red, and the fluorescence quantum yields increased upon increasing the solvent polarity from nonpolar hexane to polar dimethyl sulfoxide. Due to the formed random nanostructured aggregates, the compounds exhibited AIE characteristics in THF/H₂O mixtures. Oppositely, their emission quenched 0D particles which were afforded by quick evaporation of their dichloromethane solvents under vacuum displayed remarkable mechanoresponsive luminescence turn-on behavior. Our results suggest that rationally design ICT molecules and control their nanostructures would be promising way for realizing multifunctional fluorescent materials.

Full text of DOI:10.1016/j.dyepig.2018.03.059

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Accepted Manuscript
1, 3-Indanedione functionalized fluorene luminophores: Negative solvatochromism,
nanostructure-morphology determined AIE and mechanoresponsive luminescence
turn-on
Fang Zhang, Rong Zhang, Xiaozhong Liang, Kunpeng Guo, Zhaoxiang Han, Xiaoqing
Lu, Jingjuan Xie, Jie Li, Da Li, Xia Tian
PII:
S0143-7208(18)30226-2
10.1016/j.dyepig.2018.03.059
DYPI 6644
DOI:
Reference:
To appear in: Dyes and Pigments
Received Date: 30 January 2018
Revised Date: 24 March 2018
Accepted Date: 24 March 2018
Please cite this article as: Zhang F, Zhang R, Liang X, Guo K, Han Z, Lu X, Xie J, Li J, Li D, Tian X,
1, 3-Indanedione functionalized fluorene luminophores: Negative solvatochromism, nanostructure-
morphology determined AIE and mechanoresponsive luminescence turn-on, Dyes and Pigments (2018),
doi: 10.1016/j.dyepig.2018.03.059.
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ACCEPTED MANUSCRIPT
Graphical Abstract
A series of 1, 3-indanedione functionalized fluorene luminophores simultaneously
exhibit negative solvatochromism, AIE and mechanoresponsive luminescence
turn-on were realized by taking the advantages of ICT and nanostructured
morphological effects
.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.
ACCEPTED MANUSCRIPT
1, 3-Indanedione functionalized fluorene luminophores: Negative
solvatochromism, nanostructure-morphology determined AIE and
mechanoresponsive luminescence turn-on
Fang Zhang, a Rong Zhang, a Xiaozhong Liang, a Kunpeng Guo, a* Zhaoxiang Han, b
Xiaoqing Lu, b Jingjuan Xie, a Jie Li, a* Da Li, a Xia Tian a
a Ministry of Education Key Laboratory of Interface Science and Engineering in
Advanced Materials, Research Center of Advanced Materials Science and Technology,
Taiyuan University of Technology, Taiyuan 030024, P. R. China
b College of Science, China University of Petroleum, Qingdao, Shandong 266555,
China.
Corresponding Author: guokunpeng@tyut.edu.cn; lijie01@tyut.edu.cn
Abstract
Luminous efficiency in polar environment and aggregated state, as well as
high-contrast luminescence on/off switching under external stimuli are significant
issues to be addressed in developing functional fluorescent materials. Combining the
advantages of solvatochromic effect in intramolecular charge transfer (ICT)
compounds with their nanostructured morphological effects, we herein report a series
of A–π–D–π–A fluorene derivatives, which simultaneously exhibit negative
solvatochromism, aggregation-induced emission (AIE) and mechanoresponsive
luminescence (MRL) turn-on. These molecules contain the same fluorene donor (D)
and 1,3-indandione acceptor (A) but differ in alkyl substituents in the 9-position of the
fluorene segment, including 9,9-dibutyl (b-DIPF), 9,9-dioctyl (o-DIPF) and
9,9-didodecyl (d-DIPF). The emission colors of these compounds were changed from
1

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.
ACCEPTED MANUSCRIPT
blue to orange-red, and the fluorescence quantum yields increased upon increasing the
solvent polarity from nonpolar hexane to polar dimethyl sulfoxide. Due to the formed
random nanostructured aggregates, the compounds exhibited AIE characteristics in
THF/H2O mixtures. Oppositely, their emission quenched 0D particles which were
afforded by quick evaporation of their dichloromethane solvents under vacuum
displayed remarkable mechanoresponsive luminescence turn-on behavior. Our results
suggest that rationally design ICT molecules and control their nanostructures would
be promising way for realizing multifunctional fluorescent materials.
KEYWORDS: organic luminophores; nanostructure morphology; negative
solvatochromism; aggregation-induced emission; mechanoresponsive luminescence
turn-on
1. Introduction
Luminescent materials that not only give intense emission in both solvents and
aggregate state, but also exhibit sensitive luminescent properties to external stimuli
have attracted great interest due to their potential application in sensors, displays,
memory storage and security technologies [1−4]. Among them, organic molecules
with tunable donor (D) and acceptor (A) segments are promising candidates owning
to their inherent intramolecular charge transfer (ICT) character and tunable molecular
conformations based on which the modification of the intermolecular interactions in
response to external stimuli could be realized [5−8]. Recently, some polarity-sensitive
ICT fluorescent probes whose emitting colors can be tuned in a wide range of
wavelengths are available [9−12]. However, most of the reported compounds exhibit
2