Design, synthesis and aggregation induced emission properties of two bichromophores with a triphenylamine-coumarin dyad structure

Article abstract of DOI:10.1016/j.dyepig.2017.07.046

On the basis of molecular design about the donor-acceptor (D-A) triphenylamine-coumarin (TPA-coumarin) dyad, two new bichromophores 7-butoxy-6-(4-(diphenylamino)phenyl)-4,8-dimethyl-2H-chromen-2-one (TC) and 7-butoxy-6-(4-(diphenylamino)phenyl)-8-methyl-4-(trifluoromethyl)-2H-chromen-2-one (TF), were synthesized and characterized by using IR, ¹H NMR, ¹³C NMR and HRMS. Both TC and TF exhibited the expected solid-state fluorescence emission due to the aggregation induced emission effect and different degrees of positive solvatochromism due to their different molecular conformations in various solvents. Owing to the different push-pull electronic effects of substituents on the coumarin moiety, TC and TF, acting as the D-A compounds, showed different HOMO-LUMO gaps and a variable red-shifted emission in their solid-state, substantiating the possibility to effectively tune the photophysical properties of these bichromophores by rational molecular design.

Full text of DOI:10.1016/j.dyepig.2017.07.046

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Accepted Manuscript
Design, synthesis and aggregation induced emission properties of two
bichromophores with a triphenylamine-coumarin dyad structure
Han Yan, Xinlei Meng, Baoyan Li, Shusheng Ge, Yun Lu
PII:
S0143-7208(17)30967-1
10.1016/j.dyepig.2017.07.046
DYPI 6135
DOI:
Reference:
To appear in: Dyes and Pigments
Received Date: 26 April 2017
Revised Date: 20 July 2017
Accepted Date: 20 July 2017
Please cite this article as: Yan H, Meng X, Li B, Ge S, Lu Y, Design, synthesis and aggregation induced
emission properties of two bichromophores with a triphenylamine-coumarin dyad structure, Dyes and
Pigments (2017), doi: 10.1016/j.dyepig.2017.07.046.
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ACCEPTED MANUSCRIPT
1
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3
Design, synthesis and aggregation induced
emission properties of two bichromophores
with a triphenylamine-coumarin dyad
4
5
structure
Han Yan, Xinlei Meng, Baoyan Li, Shusheng Ge, Yun Lu*
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Department of Polymer Science and Engineering, State Key Laboratory of
Coordination Chemistry, Collaborative Innovation Center of Chemistry for Life
Sciences, Key Laboratory of High Performance Polymer Materials and Technology
(Nanjing University), Ministry of Education, School of Chemistry and Chemical
Engineering, Nanjing University, Nanjing 210093, P. R. China
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*Author to whom correspondence should be addressed: Nanjing University, Nanjing
210023, China
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*Corresponding author.
E-mail: yunlu@nju.edu.cn
15 ABSTRACT
16 On the basis of molecular design about the donor-acceptor (D-A)
17 triphenylamine-coumarin
18 bichromophores
(TPA-coumarin)
dyad,
two
new
19 7-butoxy-6-(4-(diphenylamino)phenyl)-4,8-dimethyl-2H-chromen-2-one
20 (TC)
and
21 7-butoxy-6-(4-(diphenylamino)phenyl)-8-methyl-4-(trifluoromethyl)-2H-
22 chromen-2-one (TF), were synthesized and characterized by using IR, 1H
13
23 NMR, C NMR and HRMS. Both TC and TF exhibited the expected

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.
ACCEPTED MANUSCRIPT
24 solid-state fluorescence emission due to the aggregation induced emission
25 effect and different degrees of positive solvatochromism due to their
26 different molecular conformations in various solvents. Owing to the
27 different push-pull electronic effects of substituents on the coumarin
28 moiety, TC and TF, acting as the D-A compounds, showed different
29 HOMO-LUMO gaps and a variable red-shifted emission in their
30 solid-state, substantiating the possibility to effectively tune the
31 photophysical properties of these bichromophores by rational molecular
32 design.
33 Keywords: Coumarin; Aggregation induced emission; Push-pull
34 chromophores; Solvatochromism; TICT; Density function theory.
35 1. Introduction
36
Over the past decades, fluorescent materials with multifunctionality,
37 such as high luminescent efficiency, fast charge transporting capacity,
38 optical waveguiding, and excellent organic light-emitting diode (OLED)
39 or field effect transistor (FET) performance, have drawn increasing
40 attention in the multiple hi-tech applications [1-7]. As a class of efficient
41 luminescent compounds, coumarins showed a series of excellent
42 properties, for example, high quantum yields (up to 0.90), high molar
43 extinction coefficients (10,000-40,000) [8-11], large Stokes shifts (up to
44 160 nm) [12] and the responsiveness to the changes of the environment
45 polarity [13-15], thus can be used as dyes [16,17], solvatochromic probes,