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Metal selective co-ordinative self-assembly of π-donors

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Abstract

Metal selective co-ordinative nanostructures were constructed by the supramolecular co-assembly of pyridine appended TTF (TTF-Py) and pyrene (PYR-Py) derivatives in appropriate solvent composition mixtures with metal ions. Microscopic analyses show that TTF-Py shows distinctive morphology with either of these metal ions, forming I-D tapes with 1:1 Pb2 +  complex and 2-D sheets with 1:2 Zn2 +  complex. A rationale has been provided from molecular level packing for such hierarchical changes. In case of Cu2 + , we have observed an anomalous binding of metal ion to the core sulphur groups causing redox changes in the TTF core. PYR-Py on the other hand is shown to be a fluorescent sensor for Pb2 + , Zn2 + , Hg2 +  and Ag + . With different fluorescent response for metal complexes, we essentially obtained similar 1-D assemblies suggesting similar binding modes for all of them. Supramolecular approach through which morphology of an electron donor moiety can be engineered by metal ions can be a new tool in nanoelectronics.

Metal selective self-assembly of pyridine appended donors moieties of TTF and Pyrene, to various nanostructures is presented. The supramolecular morphology is greatly dependent on the metal ion and a direct correlation of binding mode with the nanostructures is observed.

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References

  1. (a) Ajayaghosh A, George S J and Schenning A P H J 2005 in Topics in current chemistry, vol. 258, (Ed: F Würthner), Springer, pp. 83; (b) Babu S S, Kartha K K and Ajayaghosh A 2010 J. Phys. Chem. Lett. 1 3413; (c) Ajayaghosh A, Praveen V K 2007 Acc. Chem. Res. 40 644

  2. (a) Brunsveld L, Folmer B J B, Meijer E W and Sijbesma R P 2001 Chem. Rev. 101 4071; (b) Whitesides G M, Mathias J P and Seto C T 1991 Science 254 1312; (c) Prins L J, Reinhoudt D N and Timmerman P 2001 Angew. Chem., Int. Ed. 40 2382; (d) Shimizu T, Masuda M and Minamikawa H 2005 Chem. Rev. 105 1401; (e) Yan Q, Yiyang L, Yijie W, Zhiyi Y, Jun L, Jiang Z, Yun Y and Jianbin H 2009 Nano Lett. 9 4500

  3. (a) Schoonbeek F S, van Esch J, Wegewijs B, Rep D B A, de Haas M P, Klapwijk T M, Kellogg R M and Feringa B L 1999 Angew. Chem., Int. Ed. 38 1393; (b) Swager T M, Gil C J and Wrighton M S 1995 J. Phys. Chem. 99 4886

  4. (a) George S J and Ajayaghosh A 2001 J. Am. Chem. Soc. 123 5148; (b) George S J and Ajayaghosh A 2005 Chem. Eur. J. 11 3217; (c) Babu P, Sangeetha N M, Vijaykumar P, Maitra U, Rissanen K and Raju A R 2003 Chem. Eur. J. 9 1922; (d) Hoeben F J M, Jonkheijm P, Meijer E W and Schenning A P H J 2005 Chem. Rev. 105 1491; (e) Samanta S K, Pal A and Bhattacharya S 2009 Langmuir 25 8567; (f) Bhattacharya S and Samanta S K 2009 Langmuir 25 8378; (g) Prasanthkumar S, Saeki A, Seki S and Ajayaghosh A 2010 J. Am. Chem. Soc. 132 8866; (h) Prasanthkumar S, Gopal A and Ajayaghosh A 2010 J. Am. Chem. Soc. 132 13206; (i) Ajayaghosh A, Varghese R, Praveen V K and Mahesh S 2006 Angew. Chem. Int. Ed. 45 3261; (j) Yagai S, Mahesh S, Kikkawa Y, Unoike K, Karatsu T, Kitamura A and Ajayaghosh A 2008 Angew. Chem. 120 4769

  5. (a) Oh M and Mirkin C A 2005 Nature 438 651; (b) Sun X, Dong S and Wang E 2005 J. Am. Chem. Soc. 127 13102; (c) Oh M and Mirkin C A 2006 Angew. Chem., Int. Ed. 118 5618; (d) Maeda H, Hasegawa M, Hashimoto T, Kakimoto T, Nishio S and Nakanishi T 2006 J. Am. Chem. Soc. 128 10024

  6. (a) Würthner F, Stepanenko V and Sautter A 2006 Angew. Chem., Int. Ed. 118 1973; (b) Jeon Y-M, Heo J and Mirkin C A 2007 J. Am. Chem. Soc. 129 7480

    Google Scholar 

  7. (a) Kim Y, Mayer M F and Zimmerman S C 2003 Angew. Chem., Int. Ed. 115 1153; (b) Liu B, Qian D-J, Chen M, Wakayama T, Nakamura C and Miyake J 2006 Chem. Commun. 30 3175

  8. Kim H-J, Lee E, Park H-S, Lee M 2007 J. Am. Chem. Soc. 129 10994

    Article  CAS  Google Scholar 

  9. (a) Geng Y, Wang X-J, Chen B, Xue H, Zhao Y-P, Lee S, Tung C-H and Wu L-Z 2009 Chem. Eur. J. 15 51241; (b) Xue H, Tang X-J, Wu L-Z, Zhang L-P and Tung C-H 2005 J. Org. Chem. 70 9727; (c) Ajayaghosh A, Chithra P, Varghese R 2007 Angew. Chem., Int. Ed. 46 230; (d) Ajayaghosh A, Chithra P, Varghese R and Divya K P 2008 Chem. Commun. 8 969; (e) Sreejith S, Divya K P and Ajayaghosh A 2008 Chem. Commun. 25 2903; (f) Chithra P, Varghese R, Divya K P and Ajayaghosh A 2008 Chem. Asian J. 3 1365

  10. (a) Wang J–Y, Yan J, Ding L, Ma Y and Pei J 2009 Adv. Funct. Mater. 19 1746; (b) Kitamura T, Nakaso S, Mizoshita N, Tochigi Y, Shimomura T, Moriyama M and Kato T 2005 J. Am. Chem. Soc. 127 14769; (c) Luis Puigmarti J, Laukhin V, del Pino Á P, Gancendo J V, Rovira C, Laukhina E and Amabilino D B 2007 Angew. Chem. Int. Ed. 46 238; (d) Danila I, Riobé F, Luis J P–, del Pino Á P, Wallis J D, Amabilino D B and Avarvari N 2009 J. Mater. Chem. 19 4495; (e) Tatewaki Y, Hatanaka T, Tsunashima R, Nakamura T, Kimura M and Shirai H 2009 Chem. Asian J. 4 1474; (f) Mukhopadhyay P, Iwashita Y, Shirakawa M, Kawano S–i, Fujita N and Shinkai S 2006 Angew. Chem. Int. Ed. 45 1592; (g) Xiao J, Yin Z, Li H, Zhang Q, Boey F, Zhang H and Zhang Q J 2010 J. Am. Chem. Soc. 132 6926

  11. (a) Kitahara T, Shirakawa M, Kawano S, Beginn U, Fujita N and Shinkai S 2005 J. Am. Chem. Soc. 127 14980; (b) Wang C, Zhang D and Zhu D 2005 J. Am. Chem. Soc. 127 16372

  12. (a) Wang C, Guo Y, Wang Y, Xu H, Wang R and Zhang X 2009 Angew. Chem. Int. Ed. 48 8962; (b) Wang C, Yin S, Chen S, Xu H, Wang Z and Zhang X 2008 Angew. Chem. Int. Ed. 47 9049; (c) Das R K, Kandanelli R, Linnanto J, Bose K and Maitra U 2010 Langmuir 26 16141

  13. (a) Green D C 1979 J. Org. Chem. 44 1476; (b) Blanchard P, Salle M, Duguay G, Jubault M and Gorgues A 1992 Tetrahedron Lett. 33 2685; (c) Gorgues A Hudhomme P and Salle M 2004 Chem. Rev. 104 5151

  14. Abdel–Mottaleb M M S, Gomar–Nadal E, Surin M, Uji–i H, Mamdouh W, Veciana J, Lemaur V, Rovira C, Cornil J, Lazzaroni R, Amabilino D B, De Feyter S and De Schryver F C 2005 J. Mater. Chem. 15 4601

    Article  Google Scholar 

  15. Xu C-H, Sun W, Zhang C, Zhou C, Fang C-J and Yan C-H 2009 Chem. Eur. J. 15 8717

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Supramolecular Chemistry Laboratory, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore, 560064, India

    ANKIT JAIN, K VENKATA RAO, ANKITA GOSWAMI & SUBI J GEORGE

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  1. ANKIT JAIN
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  2. K VENKATA RAO
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JAIN, A., VENKATA RAO, K., GOSWAMI, A. et al. Metal selective co-ordinative self-assembly of π-donors. J Chem Sci 123, 773–781 (2011). https://doi.org/10.1007/s12039-011-0163-7

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