**Author details**

The formation of such complex at the border we confirmed by means of spectroscopic method. The conformation of first step is based on result we have got for membrane modified with

An Integrated View of the Molecular Recognition and Toxinology - From Analytical Procedures to Biomedical

The results we observed for bromo- and azobenzo- derivatives of investigated undecylca‐ lix[4]resorcinarene showing that the accessibility of phenols groups is very important param‐ eter for intermolecular recognition processes which are going between investigated ligands

The weakest response we have observed in case of membranes modified with ligand which has in its structure trihydroxybenzene was explained by possibilities to form the network of intramolecular hydrogen bonds. This is a relatively strong energetic barrier for the described

The second step of proposed mechanism relays on transfer of protons from water phase to organic one. This is supported by fact that independently on the host structure, the strongest signal we have observed for the strongest base between guest compounds under study. The

We have presented the systematic research on the potentiometric response of membranes modified with macrocyclic compounds containing in their structures amino groups stimulated by the undissociated phenol derivatives and membranes modified with macrocycles contain‐

The results showed that membranes modified with calix[4]pyrrole, calix[4]phyrin and corrole derivatives are able to generate an anionic potentiometric response after stimulation with undissociated forms of phenols derivatives, whereas the membranes modified with undecyl‐ calix[4]resorcinarene derivatives are able to generate the cationic potentiometric response after stimulation with unprotonated aniline derivatives. Our experimental date indicated that in two types of membranes the movement of protons across the interface is responsible for

The general mechanism of the potentiometric signal generated by membranes modified with

**•** the formation of supramolecular host -guest complex at the liquid membrane/water

**•** the transfer of protons from water surface to organic phase surface generated cationic response, whereas transfer of proton from surface of organic phase to the surface of water

In both of cases the acidity of host and basicity of guest are crucial parameters for course of

results we have got showed that lipophilicity of analytes it is not crucial parameter.

ing the phenolic groups stimulated by unprotonated derivatives of aniline.

discussed host molecules stimulated by uncharged guest relies on:

ligand 1 in which the acidity of phenolic groups is the highest.

and analytes.

Applications

510

phenomenon.

**6. Conclusions**

potentiometric signal generation.

generate of anionic response.

processes under discussion.

interface

Jerzy Radecki\* and Hanna Radecka

\*Address all correspondence to: j.radecki@pan.olsztyn.pl

Institute of Animal Reproduction and Food Research of Polish Academy of Sciences, Olsz‐ tyn, Poland

## **References**

	- [12] Radecka, H., Szymañska, I., Pietraszkiewicz, M., Pietraszkiewicz, O., Aoki, H., Ume‐ zawa, Y. *Chem. Anal. (Warsaw),* 2005, 50, 85-102.

[31] Camiolo, S., Coles, S.J., , Gale, P.A., Hursthouse, M.B., Sessler, J.L., *Acta Crystallogr. Sect.*

Potentiometry for Study of Supramolecular Recognition Processes Between Uncharged Molecules

http://dx.doi.org/10.5772/52803

513

[32] Mahammed, A., Weaver, J.J., Gray, H. B., Abdelas , M., Gross, Z., *Tetrahedron Letters,*

[34] Broadhurst, M.J., Grieg, R., Shelton, G., Johson, A.W. *J. Chem.Soc. Perkin Trans I* 1972,

[38] Piotrowski, T., Szymańska, I., Radecka, H., Radecki, J., Pietraszkiewicz, M., Pietrasz‐

[39] Szymańska, I., Radecka, H., Radecki, J., Pietraszkiewicz, M., Pietraszkiewicz, O.,

[40] Szymańska, I., Radecka, H., Radecki, J., Pietraszkiewicz, M., Pietraszkiewicz , O.

[42] Stenka, I., Radecka, H., Radecki, J., Dolusic, E., Dehaen, W. *Pol. J. Food Nutr. Sci.,* 2003,

[44] Tohda, K., Higuchi, T., Dragoe, D., Umezawa, Y., *Analytical Sciences*, 2001, 17, 833.

[45] Amemiya, S., Bühlmann, P., Pretsch, E., Rusterholz, B., Umezawa, Y., *Anal. Chem.* 2000,

[46] Bühlmann, P., Yajima, S., Tohda, K., Umezawa, K., Nishizawa, S., Umezawa, Y.,

[47] Chaniotakis, N., Chasser, A., Meyerhoff, M.E., Grovers, J. *Anal. Chem*. 1988, 60, 185.

[48] Kibbey, C.E, Park, S.B., DeAdwyler, G., Meyerhoff, M.E., *J Electroanal. Chem.*, 1999, 335

[49] Woods, C.J., Camiolo, S., Light, M.E., Coles, S.J., Hursthouse, M.B., King, M.A., Gale,

[51] Ammico, D.A, Di Natale, C., Polasse, R., Macagnanon, A., Mantini A. *Sens. Actuator B*

[36] Dimitrienko, S.G., Myshak, E. N., Pyatkova, L. N., *Talanta* , 1999, 49, 309.

kiewicz, O., Wojciechowski, K., *Electroanalysis* , 2000 , 12, 1397.

*Combinatorial Chemistry & High Throughput Screening ,* 2000, 3, 509.

[41] Asokan, C.V., Smeets, S., Dehaen, W., *Tetrahedron Lett.,* 2001, 42, 448.

[43] Aakeröy, C.B., Seddon, K.R., *Chem. Soc. Rev.,* 1993, 22,397-407.

P.A., Essex, J.W., *J. Am. Chem. Soc.,* 2002, 124, 8644.

[50] Beer, P.D., Cadman, J. *Coord. Chem. Rev.* 2003, 240, 131- 155.

*E,* 2001, 75, 816.

2003, 44, 2077.

143.

53, 127.

72, 1618

135-194.

2000, 65, 209-215.

*Electroanalysis,* 1995, 7, 811

[33] Jonson, A., W,. Kay, I.T*. J. Chem. Soc*. 1965, 1620.

[35] Wroński, M. J., *Chromatogr. A,* 1997 , 772, 19.

*Electroanalysis* , 2003 , 15, 294-302.

[37] Leo, A., Hansch, C., Elkins, D., *Chem Rev.* 1971, 71, 525.


[12] Radecka, H., Szymañska, I., Pietraszkiewicz, M., Pietraszkiewicz, O., Aoki, H., Ume‐

An Integrated View of the Molecular Recognition and Toxinology - From Analytical Procedures to Biomedical

[13] Szymañska, I., Radecka, H.,.Radecki, J., Gale, P.A., Warriner, C.N. *Journal of Electroa‐*

[14] Radecki, J., Stenka, I., Dolusic, E., Dehaen, W., Plavec, J. *Comb. Chem. High. Throughput*

[16] Piotrowski, T., Radecka, H., Radecki, J., Depraetere, S., Dehaen, W. *Electroanalysis* 2001,

[17] Radecki, J., Radecka, H., Piotrowski, T., Depraetere, S., Dehaen, W., Plavec, J. *Electroa‐*

[18] Szymañska, I., Orlewska, Cz., Janssen, D., Dehaen, W., Radecka, H. *Electrochimica*

[19] Piotrowski, T., Radecka, H., Radecki, J., Depraetere, S., Dehaen, W., *Material Science and*

[20] Piotrowski, T., Radecka, H., Radecki, J., Depraetere, S., Dehaen, W., *Anal. Letters* 2002,

[21] Radecki, J., Stenka, I., Dolusic, E., Dehaen, W., *Electrochimica Acta* 2006, 51, 2282-2288.

[22] Saraswathyamma, B., Pająk, M., Radecki, J., Maes, W., Dehaen, W., Kumar, K.G.,

[23] Saraswathyamma, B., Grzybowska, I., Orlewska, Cz., Radecki, J., Dehaen, W., Kumar,

[24] Ocicka, K., Radecka,H., Radecki, J., Pietraszkiewicz, M., Pietraszkiewicz O. *Sensors and*

[25] Poduval, R.,. Kurzątkowska, K., Stobiecka, M., Dehaen, W.F.A., Dehaen, W., Radecka,

[26] Gale, P., A., Anzenbacher Jr, P., Sessler, J., L., *Coordination Chemistry Reviews,* 2001, 222,

[28] Custelcean, R., Delmau, L.H., Moyer, B.A., Sessler J.L., Cho, W.S., Gross, D., Bates, G.W.,

[30] Bucher, Ch., Zimmerman, R.S., Lynch, V., Kral, V., Sessler, J. L., *J.Am.Chem Soc* 2001 ,

[27] Sessler, J. L., Camiolo, S., Gale, P. A., *Coordination Chemistry Reviews,* 2003, 240, 17.

Radecka, H. *Electroanalysis*, 2008, 20, No. 18, 2009 – 2015.

K.G., Radecka, H. *Electroanalysis*, 2008, 20, No. 21, 2317-2323.

H., Radecki, J. *Supramolecular Chemistry*, 2010, 22, No. 7-8, 412 – 418.

Brooks, S.J., Light, M.E., Gale, P.A., *Angew. Chem.,* 2005, 117, 2593.

[29] Gale, P.A., Sessler, J.L., Král, Lynch, V., *J. Am. Chem.Soc.,* 1996, 118, 5140.

[15] Radecki, J. Radecka , H., *Current Topice In Electrochemistry,* 2008, 13, 27-35.

zawa, Y. *Chem. Anal. (Warsaw),* 2005, 50, 85-102.

*nalytical Chemistry*, 2006, 591, 223-228.

*Screening* 2004, 7,375-381.

*nalysis* 2004, 16, 2073-2081.

*Acta* 2008, 53, 7932 - 7940.

*Engineering* 2001, 18, 223-228.

*Actuators B,* 2003, 217-224.

13, 342-346.

Applications

512

35, 1895-1906.

57.

123, 2099-2100.

	- [52] Kurzatkowska, K., Radecka, H., Dehaen, W., Wasowicz, M., Grzybowska, I. *J. Comb. Chem. Throughput. Screen.* 2007, 10, 604 – 6010.

**Chapter 21**

**Molecular Recognition of Trans-Chiral Schiff Base**

Schiff base is one of the most popular ligands in the field of coordination chemistry [1-5]. Conventionally, transition metal complexes having Schiff base ligands have been investigat‐ ed about stereochemistry and corresponding electronic properties mainly. For example, sol‐ ution paramagnetism of Ni(II) complexes, structural phase transition of Cu(II) complexes, chiral catalysts, and some types of molecule-based magnets and other interesting facts about correlation between structures and properties are known and these facts are cooperative ef‐ fect involving intermolecular interactions and molecular recognition. Because of developing importance as functional chiral materials, many researchers have investigated crystal struc‐ tures (including thermally-induced structural phase transition and polymorphism by sol‐ vents) of *trans*-type chiral Schiff base metal complexes and extract important features of

As mentioned in Abstract section, we have tested observation of some novel phenomena as‐ sociated with chirality or CD spectroscopy based on intermolecular interactions. Induced CD on various nano-scaled (inorganic) materials from chiral Schiff base metal complexes is one of them and not only electronic and magnetic dipole moments but also molecular recog‐ nition between chiral compounds and nano-scaled materials are important factors for these phenomena [6, 7]. For example, we have observed induced CD peaks from chiral Schiff base Ni(II) complexes at d-d region for achiral or chiral Schiff base Cu(II) complexes (without ex‐ changing ligands) [8], at d-d and CT regions for Cu(II)-coordinated metallodendrimers (PA‐ MAM), and surface plasmon region for Cu-clusters prepared in PAMAM by irradiation of UV light for the first time [9, 10]. In this way, we have also reported on induced CD peaks of metal complexes (both achiral and chiral ones), organometallics (ferrocene) [11], metalloden‐ drimers, metal nano-clusters, and nano-particles [9, 10] of metal-semiconductors [12]. Addi‐

> © 2013 Akitsu and Kominato; licensee InTech. This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

© 2013 Akitsu and Kominato; licensee InTech. This is a paper distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use,

distribution, and reproduction in any medium, provided the original work is properly cited.

**Metal Complexes for Induced CD**

Takashiro Akitsu and Chigusa Kominato

chiral molecular recognition in the solid states.

http://dx.doi.org/10.5772/52226

**1. Introduction**

Additional information is available at the end of the chapter

