Detection of Amine Vapors using Luminescent Xerogels from Supramolecular Metal-Containing

1.

(a) T. Gao, E. S. Tillman, N. S. Lewis, Chem. Mater. 2005,

17, 2904–2911; (b) J. M. Landete, B. Rivas, A. Marcobal,

R. Muñoz, Int. J. Food Microbiol. 2007, 117, 258–269; (c)

V. P. Aneja, P. A. Roelle, G. C. Murray, J. Scutherland, J.

W. Erisman, D. Faler, W. A. H. Asman, N. Patni, Atmos.

Environ. 2001, 35, 1903–1911; (d) P. Boeker, G. Horner, S.

Rosler, Sens. Actuators B 2000, 70, 37–42; (e) T.

Hernandezjover, M. Izquierdopulido, M. T. Veciananogues,

M. C. Vidalcarou, J. Agric. Food Chem. 1996, 44, 2710–

2715; (f) M. Nakamura, T. Sanji, M. Tanaka, Chem. Eur. J.

2011, 17, 5344–5349; (g) B. Lee, R. Scopelliti, K. Severin,

Chem. Commun. 2011, 47, 9639–9641; (h) M. Loughran,

D. Diamond, Food Chem. 2000, 69, 97–103; (i) E. Trevion,

D. Beil, H. Steinhart, Food Chem. 1997, 60, 521–526.

2.

(a) J. Kumpf, S. T. Schwaebel, U. H. F. Bunz, J. Org.

Chem. 2015, 80, 5159−5166; (b) J. Kumpf, J. Freudenberg,

S. T. Schwaebel, U. H. F. Bunz, Macromolecules 2014, 47,

2569−2573; (c) A. Mallick, B. Garai, M. A. Addicoat, P.

S. Petkov, T. Heine, R. Banerjee, Chem. Sci. 2015, 6,

1420–1425; (d) C.-F. Chow, M. H. W. Lam, W. Y. Wong,

Anal. Chem. 2013, 85, 8246−8253; (e) P. Heier, N. D.

Boscher, P. Choquet, K. Heinze, Inorg. Chem. 2014, 53,

11086−11095; (f) X. Pang, X. Yu, H. Lan, X. Ge, Y. Li, X.

Zhen, T. Yi, ACS Appl. Mater. Interfaces 2015, 7,

13569−13577; (g) H. A. Azab, S. A. El-Korashy, Z. M.

Anwar, G. M. Khairy, A. Duerkop, J. Photochem.

Photobiol. A: Chem. 2012, 243, 41–46; (h) G. Giancane,

V. Borovkov, Y. Inoue, L. Valli, J. Colloid Interface Sci.

2012, 385, 282–284; (i) X. J. Huang, T. Y. You, T. Li, X. R.

Yang, E. K. Wang, Electroanalysis 1999, 11, 969–972; (j)

Y. M. Chung, B. Raman, K. H. Ahn, Tetrahedron 2006, 62,

11645–11651; (k) X. Yang, G. Peter, C. Hauser,

Electrophoresis 2006, 27, 468–473; (l) W. X. Zhang, Z. X.

Chen, Z. H. Yang, Phys. Chem. Chem. Phys. 2009, 11,

6263–6268; (m) L. Feng, C. J. Musto, J. W. Kemling, S. H.

Lim, K. S. Suslick, Chem. Commun. 2010, 46, 2037–2039;

(n) S. Kӧrsten, G. J. Mohr, Chem. Eur. J. 2011, 17, 969–

975.

3.

C. Wang, X. W. He, L. X. Chen, Talanta 2002, 57, 1181–

1188.

4.

C. J. Liu, J. T. Lin, S. H. Wang, J. C. Jiang, L. G. Lin,

Sensors and Actuators B, 2005, 108, 521–527.

5.

S. A. Brittle, T. H. Richardson, J. Hutchinson, C. A. Hunter,

Colloids Surf. A 2008, 321, 29–33.

6.

X. Zhang, X. Liu, R. Lu, H. Zhang, P. Gong, J. Mater.

Chem. 2012, 22, 1167–1172.

7.

Z. Zhou, Q. Wang, J. Lin, Y. Chen, C. Yang, Photochem.

Photobiol. 2012, 88, 840–843.

8.

Y. Fu, Q. He, D. Zhu, Y. Wang, Y. Gao, H. Cao, J. Cheng,

Chem. Commun. 2013, 49, 11266–11268.

9.

10.

11.

12.

13.

14.

15.

16.

17.

18.

C. F. Chow, M. H. W. Lam, W. Y. Wong, Anal. Chem. 2013,

85, 8246–8253.

P. Xue, Q. Xu, P. Gong, C. Qian., A. Ren, Y. Zhang, R. Lu,

Chem. Commun. 2013, 49, 5838–5840.

T. Han, J. W. Y. Lam, N. Zhao, M. Gao, Z. Yang, E. Zhao,

Y. Dong, B. Z. Tang, Chem. Commun. 2013, 49, 4848–

4850.

S. Rochat, T. M. Swager, Angew. Chem. Int. Ed. 2014, 53,

9792–9796.

J. Kumpf, J. Freudenberg, K. Fletcher, A. Dreuw, U. H. F.

Bunz, J. Org. Chem. 2014, 79, 6634–6645.

J. Yao, Y. Fu, W. Fan, Q. He, D. Zhu, H. Cao, J. Cheng,

RSC Adv. 2015, 5, 25125–25131.

K. Hanabusa, M. Suzuki, Bull. Chem. Soc. Jpn. 2016, 89,

174–182.

K. Hanabusa, K. Harano, M. Fujisaki, Y. Nomura, M.

Suzuki, Macromolecular Sympo. 2016, 364, 7–8.

K. Hanabusa, S. Takata, M. Fujisaki, Y. Nomura, M.

Suzuki, Bull. Chem. Soc. Jpn. 2016, 89, 1391–1401.

(a), ed. F. Fages, Low Molecular Mass Gelators; Design,

Self-Assembly, Function Springer, Berlin Heidelberg New

York, 2005; (b) P. Dastidar, Chem. Soc. Rev. 2008, 37,

2699–2715; (c) S. Banerjee, R. K. Das, U. Maitra, J. Mater.

Chem. 2009, 19, 6649–6687; (d) M. Suzuki, K. Hanabusa,

Chem. Soc. Rev. 2009, 38, 967–975; (e) M. Suzuki, K.

Hanabusa, Chem. Soc. Rev. 2010, 39, 455–463; (f) J. L. Li, X.

Y. Liu, Adv. Funct. Mater. 2010, 20, 3196–3216; (g) G.

John, B. V. Shankar, S. R. Jadhav, P. K. Vemula, Langmuir

2010, 26, 17843–17851; (h) H. Svobodová, V. Noponen, E.

Kolehmainen, E. Sievänen, RSC Adv. 2012, 2, 4985–5007;

(i) S. S. Babu, S. Prasanthkumar, A. Ajayaghosh, Angew.

Chem., Int. Ed. 2012, 51, 1766–1776; (j) A. Y. Y. Tam, V.

W. W. Yam, Chem. Soc. Rev. 2013, 42, 1540–1567; (k) J.

Raeburn, A. Z. Cardoso, D. J. Adams, Chem. Soc. Rev.

2013, 42, 5143–5156; (l) G. Yu, X. Yan, C. Han, F. Huang,

Chem. Soc. Rev. 2013, 42, 6697–6722; (m) M. D. SegarraMaset, V. J. Nebot, J. F. Miravet, B. Escuder, Chem. Soc.

Rev. 2013, 42, 7086–7098; (n) S. S. Babu, V. K. Praveen,

A. Ajayaghosh, Chem. Rev. 2014, 114, 1973–2129; (o) D.

K. Kumar, J. W. Steed, Chem. Soc. Rev. 2014, 43, 2080–

2088; (p) V. K. Praveen, C. Ranjith, N. Armaroli, Angew.

Chem., Int. Ed. 2014, 53, 365–368; (q) Y. Lan, M. G.

Corradinia, R. G. Weiss, S. R. Raghavanc, M. A. Rogers,

Chem. Soc. Rev. 2015, 44, 6035–6058; (r) K. Hanabusa,

Polym. J. 2014, 46, 776–782.

Graphical Abstract

<Title>

Detection of Amine Vapors using Luminescent Xerogels from Supramolecular Metal-Containing Gelator

<Authors' names>

Junpei Sasaki, Masahiro Suzuki, Kenji Hanabusa

<Summary>

Fluorescent gelators containing a tris(-diketonato) complex are synthesized by using gelation-driving chelates, and their gelation

abilities are studied. Thin-layer films are prepared on quartz plates from the solutions and studied as chemosensors for amines. The

fluorescence-quenching efficiencies upon exposure to saturated primary and secondary amines depend on the basicity and bulkiness of

the amines rather than the vapor pressure.

<Diagram>

Vapor of amines

0.5 µm

Fl uorescence Quenching (%)

100

Supramolecular assembly of

Eu 3+-containing gelator

80

60

40

Hexylamine

Ammonia

Aniline

Naphthylamine

20

20

40

Ti me (min)

60

Fluorescence quenching of xerogel film of

Eu3+-containing gelator by amines

...