Abstract
A novel dithienylethene amide-based photoswitchable anion receptor was synthesised by amidation of 4,4′-(cyclopent-1-ene-1,2-diyl) bis(5-methylthiophene-2-carboxylic acid) with 4-nitroaniline in 56% yield under mild conditions; its structure was confirmed by NMR, MS and elemental analysis. Investigation of its photochromic properties indicated that 4,4′-(cyclopent-1-ene-1,2-diyl)bis[5-methyl-N-(4-nitrophenyl) thiophene-2-carboxamide] had good reversibility and excellent fatigue resistance upon irradiation with UV or visible light and can serve as a colorimetric sensor for fluoride, resulting in a significant change in the absorption spectrum.
References
1.
Amendola V.
,
Esteban-Gómez D.
,
Fabbrizzi L.
, and
Licchelli M.
, Acc. Chem. Res. , 2016 , 39 , 343 .
2.
Zhou Y.
,
Zhang J.F.
, and
Yoon J.
, Chem. Rev. , 2014 , 114 , 5511 .
3.
Gale P.A.
,
Garcia-Garrido S.E.
, and
Garric J.
, Chem. Soc. Rev. , 2008 , 37 , 151 .
4.
Zhou Y.
,
Xu Z.C.
, and
Yoon J.
, Chem. Soc. Rev. , 2011 , 40 , 2222 .
5.
Gunnlaugsson T.
,
Glynn M.
,
Tocci G.M.
,
Kruger P.E.
, and
Pfeffer F.M.
, Coord. Chem. Rev. , 2006 , 250 , 3094 .
6.
Gale P.A.
,
Garcia-Garrido S.E.
, and
Garric J.
, Chem. Soc. Rev. , 2008 , 37 , 151 .
7.
Kubik S.
, Chem. Soc. Rev. , 2009 , 38 , 585 .
8.
Caltagirone C.
, and
Gale P.A.
, Chem. Soc. Rev. , 2009 , 38 , 520 .
9.
Yang W.R.
,
Jaramillo D.
,
Gooding J.J.
,
Hibbert D.B.
,
Zhang R.
,
Willett G.D.
, and
Fisher K.J.
, Chem. Commun. , 2001 , 198 , 1982 .
10.
Gonzales A.
,
Firmino M.
,
Nomura C.
,
Rocha F.
,
Oliveira P.
, and
Gaubeur I.
, Anal. Chim. Acta , 2009 , 636 , 198 .
11.
Becker J.S.
,
Matusch A.
,
Depboylu C.
,
Dobrowolska J.
, and
Zoriy M.
, Anal. Chem. , 2007 , 79 , 6074 .
12.
Zhou Y.
,
Zhang J.F.
, and
Yoon J.
, Chem. Rev. , 2014 , 114 , 5511 .
13.
Duke R.M.
,
Veale E.B.
,
Pfeffer F.M.
,
Kruger P.E.
, and
Gunnlaugsson T.
, Chem. Soc. Rev. , 2010 , 39 , 3936 .
14.
Ding Y.B.
,
Zhu W.H.
, and
Xie Y.S.
, Chem. Rev. , 2017 , 117 , 2203 .
15.
Gale P.A.
, Acc. Chem. Res. , 2006 , 39 , 465 .
16.
Irie M.
, Chem. Rev. , 2000 , 100 , 1685 .
17.
Tian H.
, and
Yang S.
, Chem. Soc. Rev. , 2004 , 33 , 85 .
18.
Zhang J.
,
Wang J.
, and
Tian H.
, Mater. Horiz. , 2014 , 1 , 169 .
19.
Irie M.
,
Fukaminato T.
,
Matsuda K.
, and
Kobatake S.
, Chem. Rev. , 2014 , 114 , 12174 .
20.
Zhu S.
,
Li W.
, and
Zhu W.
, Progress Chem. , 2016 , 28 , 975 .
21.
Pu S.Z.
,
Sun Q.
,
Fan C.B.
,
Wang R.J.
, and
Liu G.
, J. Mater. Chem. C , 2016 , 4 , 3075 .
22.
Qu S.Z.
,
Zheng C.H.
,
Liao G.M.
,
Fan C.B.
,
Liu G.
, and
Pu S.Z.
, RSC Adv. , 2017 , 7 , 9833 .
23.
Zhang X.X.
,
Wang R.J.
,
Liu G.
,
Fan C.B.
, and
Pu S.Z.
, Tetrahedron , 2016 , 72 , 8449 .
24.
Takeshita T.
,
Kurata H.
, and
Hara M.
, J. Photochem. Photobio. A: Chem. , 2017 , 344 , 28 .
25.
Liu H.H.
, and
Chen Y.
, Eur. J. Org. Chem. , 2009 , 5261 .
26.
Zou Q.
,
Li X.
,
Zhang J.J.
,
Zhou J.
,
Sun B.B.
, and
Tian H.
, Chem. Commun. , 2012 , 48 , 2095 .
27.
Jia H.J.
,
Pu S.Z.
,
Fan C.B.
,
Liu G.
, and
Zheng C.H.
, Dyes Pigm. , 2015 , 121 , 211 .
28.
Hu F.
,
Cao M.
,
Ma X.
,
Liu S.H.
, and
Yin J.
, J. Org. Chem. , 2015 , 80 , 7830 .
29.
Liu W.
,
Hu F.
,
Chen Z.
,
Li Z.
,
Yin J.
,
Yu G.-A.
, and
Liu S.H.
, Dyes Pigm. , 2015 , 115 , 190 .
30.
Li Z.
,
Zhang C.
,
Ren Y.L.
,
Yin J.
, and
Liu S.H.
, Org. Lett. , 2011 , 13 , 6022 .
31.
Dubonosov A.D.
,
Bren V.A.
,
Minkin V.I.
,
Shepelenko E.N.
,
Tikhomirova K.S.
,
Starikov A.G.
, and
Revinskii Y.V.
, Tetrahedron , 2015 , 71 , 8817 .
32.
Tian Z.
,
Cui S.
, and
Pu S.
, Tetrahedron Lett. , 2016 , 57 , 2703 .
33.
Wang R.
,
Wang N.
,
Pu S.
,
Zhang X.
,
Liu G.
, and
Dai Y.
, Dyes Pigm. , 2017 , 146 , 445 .
34.
Tang X.G.
,
Liu H.L.
, and
Pu S.Z.
, Photochem. Photobiol. Sci. , 2016 , 15 , 1579 .
35.
Fu Y.
,
Fan C.
,
Liu G.
, and
Pu S.
, Sens. Actuators B , 2017 , 239 , 295 .
36.
Li Z.X.
,
Liao L.Y.
,
Sun W.
,
Xu C.H.
,
Zhang C.
, and
Fang C.
, J. Phy. Chem. C , 2008 , 112 , 5190 .
37.
Lee J.Y.
,
Cho E.J.
,
Mukamel S.
, and
Nam K.C.
, J. Org. Chem. , 2004 , 69 , 943 .
38.
Kang S.O.
,
Powell D.
,
Day V.W.
, and
Bowman-James K.
, Angew. Chem. Int. Ed. , 2006 , 45 , 1921 .
39.
Lucas L.N.
,
de Jong J.J.D.
,
van Esch J.H.
,
Kellogg R.M.
, and
Feringa B.L.
, Eur. J. Org. Chem. , 2003 , 155 .
40.
Irie M.
,
Lifka T.
,
Kobatake S.
, and
Kato N.
, J. Am. Chem. Soc. , 2000 , 122 , 4871 .