A facile design for multifunctional AIEgen based on tetraaniline derivatives
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摘要
Aniline oligomers have been widely used in many fields due to their excellent physicochemical properties. Owing to strong intermolecular interactions, their emission is always weakened or quenched when they are in high concentration or aggregated state, which greatly limits their fluorescent applications. Inspired by the concept of aggregation-induced emission(AIE), herein we introduced large steric groups onto the aniline oligomer to prevent the formation of packing structure. In particular, diphenyl vinyl group was bonded with oligomeric tetraaniline by a facile synthetic procedure with high yield. The obtained aniline oligomer derivative exhibited typical AIE features, which was also confirmed by density functional theoretical calculation. More importantly, this AIE oligomer was able to detect Fe~(3+) ions selectively and quantitatively. The fluorescence intensity decreased linearly along with the increment of Fe~(3+) concentration. Moreover, we demonstrated that this AIE oligomer could stain live bacteria, such as E. coli and S. aureus efficiently. All these results suggest that such a readily accessible and multifunctional tetraaniline derivative provides a new platform for the construction of fluorescent materials.
Aniline oligomers have been widely used in many fields due to their excellent physicochemical properties. Owing to strong intermolecular interactions, their emission is always weakened or quenched when they are in high concentration or aggregated state, which greatly limits their fluorescent applications. Inspired by the concept of aggregation-induced emission(AIE), herein we introduced large steric groups onto the aniline oligomer to prevent the formation of packing structure. In particular, diphenyl vinyl group was bonded with oligomeric tetraaniline by a facile synthetic procedure with high yield. The obtained aniline oligomer derivative exhibited typical AIE features, which was also confirmed by density functional theoretical calculation. More importantly, this AIE oligomer was able to detect Fe~(3+) ions selectively and quantitatively. The fluorescence intensity decreased linearly along with the increment of Fe~(3+) concentration. Moreover, we demonstrated that this AIE oligomer could stain live bacteria, such as E. coli and S. aureus efficiently. All these results suggest that such a readily accessible and multifunctional tetraaniline derivative provides a new platform for the construction of fluorescent materials.
Aniline oligomers have been widely used in many fields due to their excellent physicochemical properties. Owing to strong intermolecular interactions, their emission is always weakened or quenched when they are in high concentration or aggregated state, which greatly limits their fluorescent applications. Inspired by the concept of aggregation-induced emission(AIE), herein we introduced large steric groups onto the aniline oligomer to prevent the formation of packing structure. In particular, diphenyl vinyl group was bonded with oligomeric tetraaniline by a facile synthetic procedure with high yield. The obtained aniline oligomer derivative exhibited typical AIE features, which was also confirmed by density functional theoretical calculation. More importantly, this AIE oligomer was able to detect Fe~(3+) ions selectively and quantitatively. The fluorescence intensity decreased linearly along with the increment of Fe~(3+) concentration. Moreover, we demonstrated that this AIE oligomer could stain live bacteria, such as E. coli and S. aureus efficiently. All these results suggest that such a readily accessible and multifunctional tetraaniline derivative provides a new platform for the construction of fluorescent materials.
引文
1 Liang J,Tang BZ,Liu B.Chem Soc Rev,2015,44:2798-2811
2 Li Q,Li Z.Sci China Chem,2015,58:1800-1809
3 Wang ZL,Ma K,Xu B,Li X,Tian WJ.Sci China Chem,2013,56:1234-1238
4 Hong Y,Lam JWY,Tang BZ.Chem Commun,2009,1:4332
5 Luo J,Xie Z,Lam JWY,Cheng L,Tang BZ,Chen H,Qiu C,Kwok HS,Zhan X,Liu Y,Zhu D.Chem Commun,2001,0:1740-1741
6 Chen J,Law CCW,Lam JWY,Dong Y,Lo SMF,Williams ID,Zhu D,Tang BZ.Chem Mater,2003,15:1535-1546
7 Hong Y,Lam JWY,Tang BZ.Chem Soc Rev,2011,40:5361-5388
8 Dong Y,Lam JWY,Qin A,Liu J,Li Z,Tang BZ,Sun J,Kwok HS.Appl Phys Lett,2007,91:011111
9 Zhao Z,He B,Tang BZ.Chem Sci,2015,6:5347-5365
10 Li W,Chen D,Wang H,Luo S,Dong L,Zhang Y,Shi J,Tong B,Dong Y.ACS Appl Mater Interfaces,2015,7:26094-26100
11 Li R,Xiao S,Li Y,Lin Q,Zhang R,Zhao J,Yang C,Zou K,Li D,Yi T.Chem Sci,2014,5:3922-3928
12 Yang M,Zhang Y,Zhu W,Wang H,Huang J,Cheng L,Zhou H,Wu J,Tian Y.J Mater Chem C,2015,3:1994-2002
13 Zheng M,Zhang DT,Sun MX,Li YP,Liu TL,Xue SF,Yang WJ.JMater Chem C,2014,2:1913-1920
14 Gu K,Qiu W,Guo Z,Yan C,Zhu S,Yao D,Shi P,Tian H,Zhu WH.Chem Sci,2019,10:398-405
15 Shao A,Xie Y,Zhu S,Guo Z,Zhu S,Guo J,Shi P,James TD,Tian H,Zhu WH.Angew Chem Int Ed,2015,54:7275-7280
16 Han T,Feng X,Tong B,Shi J,Chen L,Zhi J,Dong Y.Chem Commun,2012,48:416-418
17 Song Y,Zong L,Zhang L,Li Z.Sci China Chem,2017,60:1596-1601
18 Li Q,Li Z.Adv Sci,2017,4:1600484
19 Chi Z,Zhang X,Xu B,Zhou X,Ma C,Zhang Y,Liu S,Xu J.Chem Soc Rev,2012,41:3878-3896
20 Mei J,Huang Y,Tian H.ACS Appl Mater Interfaces,2018,10:12217-12261
21 Qin A,Tang BZ.Sci China Chem,2018,61:879-881
22 Zhao Z,Chen B,Geng J,Chang Z,Aparicio-Ixta L,Nie H,Goh CC,Ng LG,Qin A,Ramos-Ortiz G,Liu B,Tang BZ.Part Part Syst Charact,2014,31:481-491
23 Song Z,Zhang W,Jiang M,Sung HHY,Kwok RTK,Nie H,Williams ID,Liu B,Tang BZ.Adv Funct Mater,2016,26:824-832
24 Cao L,Gong C,Yang J.Macromol Rapid Commun,2016,37:343-350
25 Huang LT,Yen HJ,Liou GS.Macromolecules,2011,44:9595-9610
26 Cao L,Gong C,Yang J.Electrochim Acta,2016,192:422-430
27 Wang E,Zhao E,Hong Y,Lam JWY,Tang BZ.J Mater Chem B,2014,2:2013-2019
28 Kang M,Gu X,Kwok RTK,Leung CWT,Lam JWY,Li F,Tang BZ.Chem Commun,2016,52:5957-5960
29 Jiang M,Gu X,Lam JWY,Zhang Y,Kwok RTK,Wong KS,Tang BZ.Chem Sci,2017,8:5440-5446
30 Wen W,Shi ZF,Cao XP,Xu NS.Dyes Pigments,2016,132:282-290
31 Shen XY,Wang YJ,Zhao E,Yuan WZ,Liu Y,Lu P,Qin A,Ma Y,Sun JZ,Tang BZ.J Phys Chem C,2013,117:7334-7347
32 Pan C,Wang K,Ji S,Wang H,Li Z,He H,Huo Y.RSC Adv,2017,7:36007-36014
33 Bian N,Chen Q,Qiu XL,Qi AD,Han BH.New J Chem,2011,35:1667-1671
34 Kaya EN,Yuksel F,?zp?nar GA?,Bulut M,Durmu?M.Sens Actuators B-Chem,2014,194:377-388
35 Wang L,Li H,Cao D.Sens Actuators B-Chem,2013,181:749-755
36 Niu Q,Sun T,Li T,Guo Z,Pang H.Sens Actuators B-Chem,2018,266:730-743
37 Shi X,Wang H,Han T,Feng X,Tong B,Shi J,Zhi J,Dong Y.J Mater Chem,2012,22:19296-19302
38 Wu WN,Mao PD,Wang Y,Mao XJ,Xu ZQ,Xu ZH,Zhao XL,Fan YC,Hou XF.Sens Actuators B-Chem,2018,258:393-401
39 Pannipara M,Al-Sehemi AG,Kalam A,Asiri AM,Arshad MN.Spectrochim Acta Part A-Mol Biomol Spectr,2017,183:84-89
40 He X,Wang X,Zhang L,Fang G,Liu J,Wang S.Sens Actuators B-Chem,2018,271:289-299
41 Zhao E,Chen Y,Wang H,Chen S,Lam JWY,Leung CWT,Hong Y,Tang BZ.ACS Appl Mater Interfaces,2015,7:7180-7188
42 Jiang G,Wang J,Yang Y,Zhang G,Liu Y,Lin H,Zhang G,Li Y,Fan X.Biosens Bioelectron,2016,85:62-67
43 Zhou Y,Liu H,Zhao N,Wang Z,Michael MZ,Xie N,Tang BZ,Tang Y.Sci China Chem,2018,61:892-897
2 Li Q,Li Z.Sci China Chem,2015,58:1800-1809
3 Wang ZL,Ma K,Xu B,Li X,Tian WJ.Sci China Chem,2013,56:1234-1238
4 Hong Y,Lam JWY,Tang BZ.Chem Commun,2009,1:4332
5 Luo J,Xie Z,Lam JWY,Cheng L,Tang BZ,Chen H,Qiu C,Kwok HS,Zhan X,Liu Y,Zhu D.Chem Commun,2001,0:1740-1741
6 Chen J,Law CCW,Lam JWY,Dong Y,Lo SMF,Williams ID,Zhu D,Tang BZ.Chem Mater,2003,15:1535-1546
7 Hong Y,Lam JWY,Tang BZ.Chem Soc Rev,2011,40:5361-5388
8 Dong Y,Lam JWY,Qin A,Liu J,Li Z,Tang BZ,Sun J,Kwok HS.Appl Phys Lett,2007,91:011111
9 Zhao Z,He B,Tang BZ.Chem Sci,2015,6:5347-5365
10 Li W,Chen D,Wang H,Luo S,Dong L,Zhang Y,Shi J,Tong B,Dong Y.ACS Appl Mater Interfaces,2015,7:26094-26100
11 Li R,Xiao S,Li Y,Lin Q,Zhang R,Zhao J,Yang C,Zou K,Li D,Yi T.Chem Sci,2014,5:3922-3928
12 Yang M,Zhang Y,Zhu W,Wang H,Huang J,Cheng L,Zhou H,Wu J,Tian Y.J Mater Chem C,2015,3:1994-2002
13 Zheng M,Zhang DT,Sun MX,Li YP,Liu TL,Xue SF,Yang WJ.JMater Chem C,2014,2:1913-1920
14 Gu K,Qiu W,Guo Z,Yan C,Zhu S,Yao D,Shi P,Tian H,Zhu WH.Chem Sci,2019,10:398-405
15 Shao A,Xie Y,Zhu S,Guo Z,Zhu S,Guo J,Shi P,James TD,Tian H,Zhu WH.Angew Chem Int Ed,2015,54:7275-7280
16 Han T,Feng X,Tong B,Shi J,Chen L,Zhi J,Dong Y.Chem Commun,2012,48:416-418
17 Song Y,Zong L,Zhang L,Li Z.Sci China Chem,2017,60:1596-1601
18 Li Q,Li Z.Adv Sci,2017,4:1600484
19 Chi Z,Zhang X,Xu B,Zhou X,Ma C,Zhang Y,Liu S,Xu J.Chem Soc Rev,2012,41:3878-3896
20 Mei J,Huang Y,Tian H.ACS Appl Mater Interfaces,2018,10:12217-12261
21 Qin A,Tang BZ.Sci China Chem,2018,61:879-881
22 Zhao Z,Chen B,Geng J,Chang Z,Aparicio-Ixta L,Nie H,Goh CC,Ng LG,Qin A,Ramos-Ortiz G,Liu B,Tang BZ.Part Part Syst Charact,2014,31:481-491
23 Song Z,Zhang W,Jiang M,Sung HHY,Kwok RTK,Nie H,Williams ID,Liu B,Tang BZ.Adv Funct Mater,2016,26:824-832
24 Cao L,Gong C,Yang J.Macromol Rapid Commun,2016,37:343-350
25 Huang LT,Yen HJ,Liou GS.Macromolecules,2011,44:9595-9610
26 Cao L,Gong C,Yang J.Electrochim Acta,2016,192:422-430
27 Wang E,Zhao E,Hong Y,Lam JWY,Tang BZ.J Mater Chem B,2014,2:2013-2019
28 Kang M,Gu X,Kwok RTK,Leung CWT,Lam JWY,Li F,Tang BZ.Chem Commun,2016,52:5957-5960
29 Jiang M,Gu X,Lam JWY,Zhang Y,Kwok RTK,Wong KS,Tang BZ.Chem Sci,2017,8:5440-5446
30 Wen W,Shi ZF,Cao XP,Xu NS.Dyes Pigments,2016,132:282-290
31 Shen XY,Wang YJ,Zhao E,Yuan WZ,Liu Y,Lu P,Qin A,Ma Y,Sun JZ,Tang BZ.J Phys Chem C,2013,117:7334-7347
32 Pan C,Wang K,Ji S,Wang H,Li Z,He H,Huo Y.RSC Adv,2017,7:36007-36014
33 Bian N,Chen Q,Qiu XL,Qi AD,Han BH.New J Chem,2011,35:1667-1671
34 Kaya EN,Yuksel F,?zp?nar GA?,Bulut M,Durmu?M.Sens Actuators B-Chem,2014,194:377-388
35 Wang L,Li H,Cao D.Sens Actuators B-Chem,2013,181:749-755
36 Niu Q,Sun T,Li T,Guo Z,Pang H.Sens Actuators B-Chem,2018,266:730-743
37 Shi X,Wang H,Han T,Feng X,Tong B,Shi J,Zhi J,Dong Y.J Mater Chem,2012,22:19296-19302
38 Wu WN,Mao PD,Wang Y,Mao XJ,Xu ZQ,Xu ZH,Zhao XL,Fan YC,Hou XF.Sens Actuators B-Chem,2018,258:393-401
39 Pannipara M,Al-Sehemi AG,Kalam A,Asiri AM,Arshad MN.Spectrochim Acta Part A-Mol Biomol Spectr,2017,183:84-89
40 He X,Wang X,Zhang L,Fang G,Liu J,Wang S.Sens Actuators B-Chem,2018,271:289-299
41 Zhao E,Chen Y,Wang H,Chen S,Lam JWY,Leung CWT,Hong Y,Tang BZ.ACS Appl Mater Interfaces,2015,7:7180-7188
42 Jiang G,Wang J,Yang Y,Zhang G,Liu Y,Lin H,Zhang G,Li Y,Fan X.Biosens Bioelectron,2016,85:62-67
43 Zhou Y,Liu H,Zhao N,Wang Z,Michael MZ,Xie N,Tang BZ,Tang Y.Sci China Chem,2018,61:892-897