J Fluoresc
4. Yadav M, Dixit P, Trivedi V, et al. (2009) Chromatographic sepa-
ration of (E)- and (Z)-isomers of entacapone and their simultaneous
quantitation in human plasma by LC-ESIMS/MS. J Chromatogr B
877:533–540
5. Li YW, Fang HW, Liang SX, Wang ZZ (2008) Simultaneous de-
termination of cis- and trans-boutendioic acid by partial least
squares-ultraviolet spectrophotometry. Chinese Journal of
Analytical Chemistry. 36:95–98
6. Dsouza RN, Pischel U, Nau WM (2011) Fluorescent dyes and their
supramolecular host/guest complexes with macrocycles in aqueous
solution. Chem Rev 111:7941–7980
7. Mandadapu V, Day AI, Ghanem A (2014) Cucurbituril: Chiral ap-
plications. Chirality 26:712–723
8. Behrend R, Meyer E, Rusche F (1905) Condensation products from
glycoluril and formaldehyde. Liebigs Ann Chem 339:1–37
9. Freeman WA, Mock WL, Shih NY (1981) Cucurbituril. J Am
Chem Soc 103:7367–7368
10. Kim J, Jung IS, Kim SY, Lee E, Kang JK, Sakamoto S, Yamaguchi
K, Kim K (2000) New cucurbituril homologues: Syntheses,
Isolation, characterization, and X-ray Crystal Structures of
cucurbit[n]uril (n = 5, 7, and 8). J Am Chem Soc 122:540–541
11. Day AI, Blanch RJ, Arnold AP, Lorenzo S, Lewis GR, Dance I
(2002) A cucurbituril-based gyroscane: A new supramolecular
form. Angew Chem Int Ed 41:275–277
12. Lee JW, Samal S, Selvapalam N, Kim HJ, Kim K (2003)
Cucurbituril homologues and Derivatives: new Opportunities in
supramolecular chemistry. Acc Chem Res 36:621–630
13. Florea M, Nau WM (2011) Strong binding of hydrocarbons to
cucurbituril Probed by fluorescent dye Displacement: A supramo-
lecular Gas-Sensing Ensemble. Angew Chem Int Ed 50:9338–9342
14. Li ZY, Sun SG, Y Liu F, Pang Y, JL F, FL S, XJ P (2012) Large
fluorescence enhancement of a hemicyanine by supramolecular in-
teraction with cucurbit[6]uril and its application as resettable logic
gates. Dyes Pigments 93:1401–1407
form hydrogen bond with the carbonyls of CB [7], at the same
time, the double bond would parallel to the naphthalene, π…π
interaction could be formed, the strong electron-withdrawing
capacity of carboxyl connected to the double bond might re-
duce naphthalene electron density further, so the fluorescence
intensity became lower and nearly quenched when 1.5 equiv-
alent of MAwas added. Due to the two carboxyls in FA are in
opposite sides, only one carboxyl group could form hydrogen
bond with carbonyls of CB [7], the FA molecule would
swing freely and could not form stable π…π interaction
with naphthalene, so the fluorescence intensity changed
inconspicuously.
In the same way, 2 ⊂ CB [7] titrated by different concen-
tration of MA and FA were showed in Fig. 7, it showed that
MA was interacted with 2 ⊂ CB [7] while FA was not too.
Conclusion
In summary, naphthalimide dye 1 and 2 had been prepared.
We constructed 1:1 naphthalimide dye ⊂ CB [7] assembly,
estimated the 1:1 assembly by fluorescent titration and veri-
1
fied their inclusion behavior through H NMR. This 1:1 as-
sembly was used as fluorescent probe to recognized MA and
FA, when it was titrated by MA, fluorescence changed greatly,
when it was titrated by FA, fluorescence almost kept the same.
In other words, we recognized FA and MA by fluorescent
titration successfully, and a novel method of cis/trans isomers
recognition was offered by us.
15. Buschmann HJ, Scholimeyer E (1997) Cucurbituril and -
Cyclodextrin as Hosts for the Complexation of Organic dyes. J
Incl Phenom Mol Recognit Chem 29:167–174
Acknowledgment This work is supported by the National Natural
Science Foundation of China (Grant NO. 21406108).
16. Kemp S, Wheate NJ, Stootman FH, Aldrich-Wright JR (2007) The
host-guest chemistry of Proflavine with cucurbit[6,7,8]urils.
Supramol Chem 19:475–484
17. Chernikova EY, Berdnikova DV, Fedorov YV, Fedorova OA
(2013) Effective Stabilization of cis-Isomer of styryl dye inside
the cucurbit[7]uril cavity. Macroheterocycles 6:234–239
18. Karcher S, Kornmuller A, Jekel M (2001) Cucurbituril for Water
Treatment. Part I: Solubility of cucurbituril and Reactive dyes.
Water Res 35:3309–3316
References
1. Hasdenteufel F (2006) Twenty years of separation of cis-trans (Z)-
(E) isomers. Sep Purif Rev 35:193–221
19. Jiao DZ, Scherman OA (2012) Isolation of cucurbit[n]uril homo-
logues with imidazolium salts in a recyclable manner. Green Chem
14:2445–2449
20. Elbert JE, Paulsen S, Robinson L, Elzey S, Klein K (2005) A study
of 4-(alkylamino)amino substituted 1,8-naphthalimide
fluoroionophores. J Photochem Photobiol A Chem 169:9–19
2. Yuan XY, Zhang M, Ng SW (2009) Perillartine. Acta Crystallo
graphica Section E 65:o2149
3. Wilson ME, Mook D, Graves F, Felger J, Bielsky IF, Wallen K
(2003) Tamoxifen is an estrogen Antagonist on Gonadotropin
Secretion and Responsiveness of the Hypothalamic–Pituitary–
Adrenal Axis in Female Monkeys. Endocrine 22:305–315