A Luminescent Dicyanodistyrylbenzene-based Liquid Crystal Polymer Network for Photochemically Patterned Photonic Composite Film
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摘要
A novel photonic composite film based on a luminescent dicyanodistyrylbenzene-based liquid crystal polymer network(LCN) was fabricated by using a silica colloidal crystal as a template. The upper part of inverse opal structure and the luminescence characteristics of dicyanodistyrylbenzene-based moiety endowed the resulting bilayer photonic film with structural color arising from coherent Bragg reflection and fluorescence properties, respectively. A fluorescence enhancement phenomenon was observed in the photonic film due to the overlap between the reflection band and emission band of the fluorescent LCN. More importantly, the photo-induced irreversible Z/E photoisomerization of dicyanodistyrylbenzene-based moiety in the photonic film led to both a reflection spectral shift and an observable fluorescence variation. On the basis of this effective phototuning process, microscopic patterning of photonic film was developed under both fluorescence mode and reflection mode. The work demonstrated here provides a new route to construct photo-responsive photonic film.
A novel photonic composite film based on a luminescent dicyanodistyrylbenzene-based liquid crystal polymer network(LCN) was fabricated by using a silica colloidal crystal as a template. The upper part of inverse opal structure and the luminescence characteristics of dicyanodistyrylbenzene-based moiety endowed the resulting bilayer photonic film with structural color arising from coherent Bragg reflection and fluorescence properties, respectively. A fluorescence enhancement phenomenon was observed in the photonic film due to the overlap between the reflection band and emission band of the fluorescent LCN. More importantly, the photo-induced irreversible Z/E photoisomerization of dicyanodistyrylbenzene-based moiety in the photonic film led to both a reflection spectral shift and an observable fluorescence variation. On the basis of this effective phototuning process, microscopic patterning of photonic film was developed under both fluorescence mode and reflection mode. The work demonstrated here provides a new route to construct photo-responsive photonic film.
A novel photonic composite film based on a luminescent dicyanodistyrylbenzene-based liquid crystal polymer network(LCN) was fabricated by using a silica colloidal crystal as a template. The upper part of inverse opal structure and the luminescence characteristics of dicyanodistyrylbenzene-based moiety endowed the resulting bilayer photonic film with structural color arising from coherent Bragg reflection and fluorescence properties, respectively. A fluorescence enhancement phenomenon was observed in the photonic film due to the overlap between the reflection band and emission band of the fluorescent LCN. More importantly, the photo-induced irreversible Z/E photoisomerization of dicyanodistyrylbenzene-based moiety in the photonic film led to both a reflection spectral shift and an observable fluorescence variation. On the basis of this effective phototuning process, microscopic patterning of photonic film was developed under both fluorescence mode and reflection mode. The work demonstrated here provides a new route to construct photo-responsive photonic film.
引文
[1] Kuang,M.X.;Wang,J.X.;Jiang,L.Bio-inspired photonic crystals with superwettability.Chem.Soc.Rev.45(24),6833-6854.
2 Xu,H.;Wu,P.;Zhu,C.;Elbaz,A.;Gu,Z.Z.Photonic crystal for gas sensing.J.Mater.Chem.C 2013,1(38),6087-6098.
3 Nucara,L.;Greco,F.;Mattoli,V.Electrically responsive photonic crystals:a review.J.Mater.Chem.C 2015,3(33),8449-8467.
4 Ge,J.P.;Yin,Y.D.Responsive photonic crystals.Angew.Chem.Int.Ed.2011,50(7),1492-522.
5 Schaffner,M.;England,G.;Kolle,M.;Aizenberg,J.;Vogel,N.Combining bottom-up self-assembly with top-down microfabrication to create hierarchical inverse opals with high structural order.Small 2015,11(34),4334-4340.
6 Ding,T.;Zhao,Q.B.;Smoukov,S.K.;Baumberg,J.J.Selectively patterning polymer opal films via microimprint lithography.Adv.Optical.Mater.2014,2(11),1098.
7 Bao,B.;Li,M.Z.;Li,Jiang,Y.K.;Gu,Z.K.;Zhang,X.Y.;Jiang,L.;Song,Y.L.Quantum dots:patterning fluorescent quantum dot nanocomposites by reactive inkjet printing.Small2015,11(14),1649-1654.
8 Sch?fer,C.G.;Gallei,M.;Zahn,J.T.;Engelhardt,J.;Hellmann,G.P.;Rehahn,M.Reversible light-,thermos-and mechanoresponsive elastomeric polymer opal films.Chem.Mater.2013,25(11),2309-2318.
9 Lee,J.S.;Je,K.;Kim,S.H.,Designing multicolored photonic micropatterns through the regioselective thermal compression of inverse opals.Adv.Funct.Mater.2016,26(25),4587-4594.
10 Liu,J.C.;Wan,L.;Zhang,M.B.;Jiang,K.J.;Song,K.;Wang,J.X.;Ikeda,T.;Jiang,L.Lithography:electrowetting-induced morphological evolution of metal-organic inverse opals toward a water-lithography approach.Adv.Funct.Mater.2017,27(7),1605221.
11 Tian,T.;Gao,N.;Gu,C.;Li,J.;Wang,H.;Lan,Y.;Yin,X.P.;Li,G.T.Chemically patterned inverse opal created by a selective photolysis modification process.ACS Appl.Mater.Interfaces 2015,7(34),19516-19525.
12 Ohm,C.;Brehmer,M.;Zentel,R.Liquid crystalline elastomers as actuators and sensors.Adv.Mater.2010,22(31),3366-3387.
13 White,T.J.;Broer,D.J.Programmable and adaptive mechanics with liquid crystal polymer networks and elastomers.Nat.Mater.2015,14(11),1087-1098.
14 de Haan,L.T.;Schenning,A.P.H.J.;Broer,D.J.Programmed morphing of liquid crystal networks.Polymer2014,55(23),5885-5896.
15 Wu,G.L.;Jiang,Y.;Xu,D.;Tang,H.;Liang,X.;Li,G.T.Thermoresponsive inverse opal films fabricated with liquid-crystal elastomers and nematic liquid crystals.Langmuir2011,27(4),1505-1509.
16 Jiang,Y.;Xu,D.;Li,X.S.;Lin,C.X.;Li,W.N.;An,Q.;Tao,C.A.;Tang,H.;Li,G.T.Electrothermally driven structural colour based on liquid crystal elastomers.J.Mater.Chem.2012,22,11943-11949.
17 Wei,W.Y.;Shi,A.S.;Wu,T.H.;Wei,J.;Guo,J.B.Thermo-responsive shape and optical memories of photonic composite films enabled by glassy liquid crystalline polymer networks.Soft Matter 2016,12(41),8534-8541.
18 Xing,H.H.;Li,J.T.;Shi,Y.;Guo,J.B.;Wei,J.Thermally driven photonic actuator based on silica opal photonic crystal with liquid crystal elastomer.ACS Appl.Mater.Interfaces2016,8(14),9440-9445.
19 Xing,H.H.;Li,J.T.;Guo,J.B.;Wei,J.Bio-inspired thermalresponsive inverse opal films with dual structural colors based on liquid crystal elastomer.J.Mater.Chem.C 2015,3(17),4424-4430.
20 Zhao,J.Q.;Liu,Y.Y.;Yu,Y.L.Dual-responsive inverse opal films based on a crosslinked liquid crystal polymer containing azobenzene.J.Mater.Chem.C 2014,2(48),10262-10267.
21 An,B.K.;Kwon,S.K.;Jung,S.D.;Park,S.Y.Enhanced emission and its switching in fluorescent organic nanoparticles.J.Am.Chem.Soc.2002,124(48),14410-14415.
22 Lu,H.B.;Zhang,S.N.;Ding,A.X.;Yuan,M.;Zhang,G.Y.;Xu,W.;Zhang,G.B.;Wang,X.H.;Qiu,L.Z.;Yang,J.X.A luminescent liquid crystal with multistimuli tunable emission colors based on different molecular packing structures.New J.Chem.2014,38(8),3429-3433.
23 Gierschner,J.;Park,S.Y.Luminescent distyrylbenzenes:tailoring molecular structure and crystalline morphology.J.Mater.Chem.C 2013,1(37),5818-5832.
24 Abadía,M.M.;Varghese,S.;Giménez,R.;Ros,M.B.Multiresponsive luminescent dicyanodistyrylbenzenes and their photochemistry in solution and in bulk.J.Mater.Chem.C 2016,4(14),2886-2893.
25 Wang,H.;Li,F.;Ravia,I.;Gao,B.R.;Li,Y.P.;Medvedev,V.;Sun,H.B.;Tessler,N.;Ma,Y.G.Cyano-substituted oligo(p-phenylene vinylene)single crystals:a promising laser material.Adv.Funct.Mater.2011,21(19),3770-3777.
26 Park,S.K.;Varghese,S.;Kim,J.H.;Yoon,S.J.;Kwon,O.K.;An,B.K.;Gierschner,J.;Park,S.Y.Tailor-made highly luminescent and ambipolar transporting organic mixed stacked charge-transfer crystals:an isometric donor–acceptor approach.J.Am.Chem.Soc.2013,135(12),4757-4764.
27 Aparicio,F.;Cherumukkil,S.;Ajayaghosh,A.;Sanchez,L.Colour-tuneable cyano-substituted divinylene arene luminogens as fluorescentπ-gelators.Langmuir 2016,32(1),284-289.
28 Wei,R.B.;He,Y.;Wang,X.G.;Keller,P.Photoluminescent nematic liquid crystalline elastomer with a thermomechanical emission variation function.Macromol.Rapid Commun.2014,35(18),1571-1577.
29 Li,J.T.;Zhang,Z.W.;Tian,J.J.;Li,G.Q.;Wei,J.;Guo,J.B.Dicyanodistyrylbenzene-based chiral fluorescence photoswitches:an emerging class of multifunctional switches for dual-mode phototunable liquid crystals.Adv.Opt.Mater.2017,5(8),1700014.
30 Kim,H.J.;Whang,D.R.;Gierschner,J.;Lee,C.H.;Park,S.Y.High-contrast red-green-blue tricolor fluorescence switching in bicomponent molecular film.Angew.Chem.Int.Ed.2015,54(14),4330-4333.
31 Li,J.J.;Chen,Y.;Yu,J.;Cheng,N.;Liu,Y.A supramolecular artificial light-harvesting system with an ultrahigh antenna effect.Adv.Mater.2017,29(30),1701905.
32 Broer,D.J.;Boven,J.;Mol,G.N.;Challa,G.In-situ photopolymerization of oriented liquid-crystalline acrylates,3.Oriented polymer networks from a mesogenic diacrylate.Makromol.Chem.1989,190(9),2255-2268.
33 Mei,J.;Leung,N.L.;Kwok,R.T.;Lam,J.W.;Tang,B.Z.Aggregation-induced emission:together we shine,united we soar.Chem.Rev.2015,115(21),11718-11940.
34 Su,X.;Sun,X.Q.;Wu,S.L.;Zhang,S.F.Manipulating the emission intensity and lifetime of Na YF4:Yb3+,Er3+simultaneously by embedding it into Cd S photonic crystals.Nanoscale 2017,9(22),7666-9673.
35 Shao,B.;Yang,Z.W.;Li,J.;Yang,J.Z.;Wang,Y.D.;Qiu,J.B.;Song,Z.G.Au nanoparticles embedded inverse opal photonic crystals as substrates for upconversion emission enhancement.J.Am.Ceram.Soc.2017,100(3),988-997.
36 Li,H.;Xu,Z.H.;Bao,B.;Sun,N.;Song,Y.L.Improving the luminescence performance of quantum dot-based photonic crystals for white-light emission.J.Mater.Chem.C 2015,4(1),39-44.
37 Li,J.;Yang,Z.;Shao,B.;Yang,J.Z.;Wang,Y.D.;Qiu,J.B.;Song,Z.G.;French,R.H.Photoluminescence enhancement of Si O2-coated La PO4:Eu3+inverse opals by surface plasmon resonance of Ag nanoparticles.J.Am.Ceram.Soc.2016,99(10),3330-3335.
38 Wang,Q.;Qiu,J.B.;Song,Z.G.;Yang,Z.W.;Yin,Z.Y.;Zhou,D.C.;Wang,S.Q.Enhancement of Tb-Yb quantum cutting emission by inverse opal photonic crystals.Opt.Mater.2016,54,229-233.
39 Huang,H.;Chen,J.B.;Yu,Y.;Shi,Z.M.;M?hwald,H.;Zhang,G.Controlled gradient colloidal photonic crystals and their optical properties.Colloid Surface A 2013,428(13),9-17.
40 Kunzelman,J.;Kinami,M.;Crenshaw,B.R.;Protasiewicz,J.D.Weder,C.Oligo(p-phenylene vinylene)s as a“New”class of piezochromic fluorophores.Adv.Mater.2008,20(1),119-122.
2 Xu,H.;Wu,P.;Zhu,C.;Elbaz,A.;Gu,Z.Z.Photonic crystal for gas sensing.J.Mater.Chem.C 2013,1(38),6087-6098.
3 Nucara,L.;Greco,F.;Mattoli,V.Electrically responsive photonic crystals:a review.J.Mater.Chem.C 2015,3(33),8449-8467.
4 Ge,J.P.;Yin,Y.D.Responsive photonic crystals.Angew.Chem.Int.Ed.2011,50(7),1492-522.
5 Schaffner,M.;England,G.;Kolle,M.;Aizenberg,J.;Vogel,N.Combining bottom-up self-assembly with top-down microfabrication to create hierarchical inverse opals with high structural order.Small 2015,11(34),4334-4340.
6 Ding,T.;Zhao,Q.B.;Smoukov,S.K.;Baumberg,J.J.Selectively patterning polymer opal films via microimprint lithography.Adv.Optical.Mater.2014,2(11),1098.
7 Bao,B.;Li,M.Z.;Li,Jiang,Y.K.;Gu,Z.K.;Zhang,X.Y.;Jiang,L.;Song,Y.L.Quantum dots:patterning fluorescent quantum dot nanocomposites by reactive inkjet printing.Small2015,11(14),1649-1654.
8 Sch?fer,C.G.;Gallei,M.;Zahn,J.T.;Engelhardt,J.;Hellmann,G.P.;Rehahn,M.Reversible light-,thermos-and mechanoresponsive elastomeric polymer opal films.Chem.Mater.2013,25(11),2309-2318.
9 Lee,J.S.;Je,K.;Kim,S.H.,Designing multicolored photonic micropatterns through the regioselective thermal compression of inverse opals.Adv.Funct.Mater.2016,26(25),4587-4594.
10 Liu,J.C.;Wan,L.;Zhang,M.B.;Jiang,K.J.;Song,K.;Wang,J.X.;Ikeda,T.;Jiang,L.Lithography:electrowetting-induced morphological evolution of metal-organic inverse opals toward a water-lithography approach.Adv.Funct.Mater.2017,27(7),1605221.
11 Tian,T.;Gao,N.;Gu,C.;Li,J.;Wang,H.;Lan,Y.;Yin,X.P.;Li,G.T.Chemically patterned inverse opal created by a selective photolysis modification process.ACS Appl.Mater.Interfaces 2015,7(34),19516-19525.
12 Ohm,C.;Brehmer,M.;Zentel,R.Liquid crystalline elastomers as actuators and sensors.Adv.Mater.2010,22(31),3366-3387.
13 White,T.J.;Broer,D.J.Programmable and adaptive mechanics with liquid crystal polymer networks and elastomers.Nat.Mater.2015,14(11),1087-1098.
14 de Haan,L.T.;Schenning,A.P.H.J.;Broer,D.J.Programmed morphing of liquid crystal networks.Polymer2014,55(23),5885-5896.
15 Wu,G.L.;Jiang,Y.;Xu,D.;Tang,H.;Liang,X.;Li,G.T.Thermoresponsive inverse opal films fabricated with liquid-crystal elastomers and nematic liquid crystals.Langmuir2011,27(4),1505-1509.
16 Jiang,Y.;Xu,D.;Li,X.S.;Lin,C.X.;Li,W.N.;An,Q.;Tao,C.A.;Tang,H.;Li,G.T.Electrothermally driven structural colour based on liquid crystal elastomers.J.Mater.Chem.2012,22,11943-11949.
17 Wei,W.Y.;Shi,A.S.;Wu,T.H.;Wei,J.;Guo,J.B.Thermo-responsive shape and optical memories of photonic composite films enabled by glassy liquid crystalline polymer networks.Soft Matter 2016,12(41),8534-8541.
18 Xing,H.H.;Li,J.T.;Shi,Y.;Guo,J.B.;Wei,J.Thermally driven photonic actuator based on silica opal photonic crystal with liquid crystal elastomer.ACS Appl.Mater.Interfaces2016,8(14),9440-9445.
19 Xing,H.H.;Li,J.T.;Guo,J.B.;Wei,J.Bio-inspired thermalresponsive inverse opal films with dual structural colors based on liquid crystal elastomer.J.Mater.Chem.C 2015,3(17),4424-4430.
20 Zhao,J.Q.;Liu,Y.Y.;Yu,Y.L.Dual-responsive inverse opal films based on a crosslinked liquid crystal polymer containing azobenzene.J.Mater.Chem.C 2014,2(48),10262-10267.
21 An,B.K.;Kwon,S.K.;Jung,S.D.;Park,S.Y.Enhanced emission and its switching in fluorescent organic nanoparticles.J.Am.Chem.Soc.2002,124(48),14410-14415.
22 Lu,H.B.;Zhang,S.N.;Ding,A.X.;Yuan,M.;Zhang,G.Y.;Xu,W.;Zhang,G.B.;Wang,X.H.;Qiu,L.Z.;Yang,J.X.A luminescent liquid crystal with multistimuli tunable emission colors based on different molecular packing structures.New J.Chem.2014,38(8),3429-3433.
23 Gierschner,J.;Park,S.Y.Luminescent distyrylbenzenes:tailoring molecular structure and crystalline morphology.J.Mater.Chem.C 2013,1(37),5818-5832.
24 Abadía,M.M.;Varghese,S.;Giménez,R.;Ros,M.B.Multiresponsive luminescent dicyanodistyrylbenzenes and their photochemistry in solution and in bulk.J.Mater.Chem.C 2016,4(14),2886-2893.
25 Wang,H.;Li,F.;Ravia,I.;Gao,B.R.;Li,Y.P.;Medvedev,V.;Sun,H.B.;Tessler,N.;Ma,Y.G.Cyano-substituted oligo(p-phenylene vinylene)single crystals:a promising laser material.Adv.Funct.Mater.2011,21(19),3770-3777.
26 Park,S.K.;Varghese,S.;Kim,J.H.;Yoon,S.J.;Kwon,O.K.;An,B.K.;Gierschner,J.;Park,S.Y.Tailor-made highly luminescent and ambipolar transporting organic mixed stacked charge-transfer crystals:an isometric donor–acceptor approach.J.Am.Chem.Soc.2013,135(12),4757-4764.
27 Aparicio,F.;Cherumukkil,S.;Ajayaghosh,A.;Sanchez,L.Colour-tuneable cyano-substituted divinylene arene luminogens as fluorescentπ-gelators.Langmuir 2016,32(1),284-289.
28 Wei,R.B.;He,Y.;Wang,X.G.;Keller,P.Photoluminescent nematic liquid crystalline elastomer with a thermomechanical emission variation function.Macromol.Rapid Commun.2014,35(18),1571-1577.
29 Li,J.T.;Zhang,Z.W.;Tian,J.J.;Li,G.Q.;Wei,J.;Guo,J.B.Dicyanodistyrylbenzene-based chiral fluorescence photoswitches:an emerging class of multifunctional switches for dual-mode phototunable liquid crystals.Adv.Opt.Mater.2017,5(8),1700014.
30 Kim,H.J.;Whang,D.R.;Gierschner,J.;Lee,C.H.;Park,S.Y.High-contrast red-green-blue tricolor fluorescence switching in bicomponent molecular film.Angew.Chem.Int.Ed.2015,54(14),4330-4333.
31 Li,J.J.;Chen,Y.;Yu,J.;Cheng,N.;Liu,Y.A supramolecular artificial light-harvesting system with an ultrahigh antenna effect.Adv.Mater.2017,29(30),1701905.
32 Broer,D.J.;Boven,J.;Mol,G.N.;Challa,G.In-situ photopolymerization of oriented liquid-crystalline acrylates,3.Oriented polymer networks from a mesogenic diacrylate.Makromol.Chem.1989,190(9),2255-2268.
33 Mei,J.;Leung,N.L.;Kwok,R.T.;Lam,J.W.;Tang,B.Z.Aggregation-induced emission:together we shine,united we soar.Chem.Rev.2015,115(21),11718-11940.
34 Su,X.;Sun,X.Q.;Wu,S.L.;Zhang,S.F.Manipulating the emission intensity and lifetime of Na YF4:Yb3+,Er3+simultaneously by embedding it into Cd S photonic crystals.Nanoscale 2017,9(22),7666-9673.
35 Shao,B.;Yang,Z.W.;Li,J.;Yang,J.Z.;Wang,Y.D.;Qiu,J.B.;Song,Z.G.Au nanoparticles embedded inverse opal photonic crystals as substrates for upconversion emission enhancement.J.Am.Ceram.Soc.2017,100(3),988-997.
36 Li,H.;Xu,Z.H.;Bao,B.;Sun,N.;Song,Y.L.Improving the luminescence performance of quantum dot-based photonic crystals for white-light emission.J.Mater.Chem.C 2015,4(1),39-44.
37 Li,J.;Yang,Z.;Shao,B.;Yang,J.Z.;Wang,Y.D.;Qiu,J.B.;Song,Z.G.;French,R.H.Photoluminescence enhancement of Si O2-coated La PO4:Eu3+inverse opals by surface plasmon resonance of Ag nanoparticles.J.Am.Ceram.Soc.2016,99(10),3330-3335.
38 Wang,Q.;Qiu,J.B.;Song,Z.G.;Yang,Z.W.;Yin,Z.Y.;Zhou,D.C.;Wang,S.Q.Enhancement of Tb-Yb quantum cutting emission by inverse opal photonic crystals.Opt.Mater.2016,54,229-233.
39 Huang,H.;Chen,J.B.;Yu,Y.;Shi,Z.M.;M?hwald,H.;Zhang,G.Controlled gradient colloidal photonic crystals and their optical properties.Colloid Surface A 2013,428(13),9-17.
40 Kunzelman,J.;Kinami,M.;Crenshaw,B.R.;Protasiewicz,J.D.Weder,C.Oligo(p-phenylene vinylene)s as a“New”class of piezochromic fluorophores.Adv.Mater.2008,20(1),119-122.