Effect of composition on the properties of novel optically active methacrylic copolymers containing side-chain zinc-porphyrin chromophores suitable to chiral recognition

Dyes and Pigments

Volumn 106, Issue , 2014, Pages 143-153

  Benelli, T ^a   Angiolini, L ^a   Caretti, D ^a   Lanzi, M ^a   Mazzocchetti, L ^a   Salatelli, E ^a   Giorgini, L ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Acid responsive materials; Chiral porphyrins; Chiral recognition; Circular dichroism; Metallated porphyrins; Polymers

Indexed keywords

AMINES; CHAINS; CHROMOPHORES; COORDINATION REACTIONS; COPOLYMERS; DICHROISM; ESTERS; MACROMOLECULES; POLYMERS; PORPHYRINS; ZINC;

ABSOLUTE CONFIGURATION; CHIRAL RECOGNITION; CHIROPTICAL PROPERTIES; CIRCULAR DICHROISM SPECTRA; COPOLYMER COMPOSITIONS; FUNCTIONAL DERIVATIVES; RADICAL COPOLYMERIZATION; RESPONSIVE MATERIALS;

ZINC COMPOUNDS;

EID: 84897374504     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2014.03.009     Document Type: Article

References (38)

1. Z. Gross, and S. Ini Remarkable effects of metal, solvent, and oxidant on metalloporphyrin-catalyzed enantioselective epoxidation of olefins J Org Chem 62 1997 5514 5521 (Pubitemid 127494900)
2. J.P. Collman, X. Zhang, V.J. Lee, E.S. Uffelman, and J.I. Brauman Regioselective and enantioselective epoxidation catalyzed by metalloporphyrins Science 261 1993 1404 1411 (Pubitemid 23334261)
3. M.O. Senge, M. Fazekas, E.G.A. Notaras, W.J. Blau, M. Zawadzka, and O.B. Locos et al. Nonlinear optical properties of porphyrins Adv Mater 19 2007 2737 2774 (Pubitemid 47603104)
4. A. Krivokapic, H.L. Anderson, G. Bourhill, R. Ives, S. Clark, and K.J. McEwan Meso-tetra-alkynyl porphyrins for optical limiting - a survey of group III and IV metal complexes Adv Mater 13 2001 652 656
5. X. Sun, D. Li, G. Chen, and J. Zhang A series of new porphyrin dyads: the synthesis and photophysical properties Dyes Pigment 71 2006 118 122 (Pubitemid 43115459)
6. J.A.B. Ferreira, V.V. Serra, A. Sánchez-Coronilla, S.M.G. Pires, M.A.F. Faustino, and A.M.S. Silva et al. The near-mid-IR HOMO-LUMO gap in amide linked porphyrin-rhodamine dyads Chem Commun 49 2013 8809 8811
7. L. Angiolini, T. Benelli, V. Cocchi, M. Lanzi, and E. Salatelli Side chain porphyrin moiety linked to polymer-fullerene composite solar cell React Funct Pol 73 2013 1198 1206
8. X. Huang, K. Nakanishi, and N. Berova Porphyrins and metalloporphyrins: versatile circular dichroic reporter groups for structural studies Chirality 12 2000 237 255 (Pubitemid 30253637)
9. N. Berova, and K. Nakanishi Exciton chirality method: principles and applications N. Berova, K. Nakanishi, R.W. Woody, Circular dichroism. Principles and applications 2000 John Wiley & Sons New York 337 382
10. M. Takeuchi, T. Imada, and S. Shinkai Highly selective and sensitive "sugar tweezer" designed from a boronic-acid-appended μ-oxobis[porphinatoiron(III)] J Am Chem Soc 118 1996 10658 10659 (Pubitemid 26381256)
11. T. Mizutani, T. Kurahashi, T. Mukakami, N. Matsumi, and H. Ogoshi An artificial receptor for dimethyl aspartate J Org Chem Soc 61 1996 539 548 (Pubitemid 26069730)
12. K. Konishi, K. Yahara, H. Toshishige, T. Aida, and S. Inoue A novel anion-binding chiral receptor based on a metalloporphyrin with molecular asymmetry. Highly enantioselective recognition of amino acid derivatives J Am Chem Soc 116 1994 1337 1344
13. M.J. Crossley, L.G. Mackay, and A.C. Try Enantioselective recognition of histidine and lysine esters by porphyrin chiral clefts and detection of amino acid conformations in the bound state J Chem Soc Chem Commun 1995 1925 1928
14. S. Arimori, M. Takeuchi, and S. Shinkai Sugar-controlled aggregate formation in boronic acid-appended porphyrin amphiphiles J Am Chem Soc 118 1996 245 246 (Pubitemid 126585645)
15. H. Imai, S. Nakagawa, and E. Kyuno Recognition of axial ligands by a zinc porphyrin host on the basis of nonpolar interligand interaction J Am Chem Soc 114 1992 6719 6723
16. X. Huang, H. Rickman, B. Borhan, N. Berova, and K. Nakanishi Zinc porphyrin tweezer in host-guest complexation:determination of absolute configurations of diamines, amino acids, and amino alcohols by circular dichroism J Am Chem Soc 120 1998 6185 6186 (Pubitemid 28307015)
17. T. Kurtàn, N. Nesna, Y.-Q. Li, X. Huang, K. Nakanishi, and N. Berova Chiral recognition by CD-sensitive dimeric zinc porphyrin host. 1. Chiroptical protocol for absolute configurational assignments of monoalcohols and primary monoamines J Am Chem Soc 123 2001 5962 5973 (Pubitemid 32888466)
18. N. Berova, G. Pescitelli, A.G. Petrovic, and G. Proni Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts Chem Commun 2009 5958 5980
19. G. Proni, G. Pescitelli, X.F. Huang, K. Nakanishi, and N. Berova Magnesium tetraarylporphyrin tweezer: a CD-sensitive host for absolute configurational assignments of α-chiral carboxylic acids J Am Chem Soc 125 2003 12914 12927 (Pubitemid 37280460)
20. M. Anyika, R. Acho, B. Borhan, H. Gholami, and K.D. Ashtekar Point to axial chirality transfer - a new probe for "sensing" the absolute configurations of mono amines J Am Chem Soc 136 2014 550 553
21. L. Angiolini, T. Benelli, and L. Giorgini Polymethacrylic zinc porphyrin: a new approach to chiral recognition React Funct Pol 71 2011 204 209
22. L. Angiolini, T. Benelli, and L. Giorgini Novel optically active methacrylic polymers containing side-chain porphyrin moieties for chiral recognition Polymer 52 2011 2747 2756
23. D.D. Perrin, W.L.F. Amarego, and D.R. Perrin Purification of laboratory chemicals 1966 Pergamon Press Oxford
24. T. Kelen, and F.J. Tüdos Analysis of the linear methods for determining copolymerizatiom reactivity ratios I. A new improved linear graphical method Macromol Sci Part A Chem 9 1975 1 27
25. S.P. Rao, S. Ponratman, S.L. Kapur, and P.K. Iyer Kelen-tüdös method applied to the analysis of high-conversion copolymerization data J Polym Sci Polym Lett Ed 14 1976 513 516
26. F.R. Mayo, and C. Walling Copolymerization Chem Rev 46 1950 191 287
27. E. Chiellini, R. Solaro, G. Galli, and A. Ledwith Optically active vinyl polymers containing fluorescent groups. 8. Synthesis and properties of copolymers of n-vinylcarbazole and (-)-menthyl acrylate and (-)-menthyl methacrylate Macromolecules 13 1980 1654 1660
28. I.R. Peat, and W.F. Reynolds Application of 13C magnetic resonance spectroscopy to the determination of the tacticity of stereoregular poly (methyl methacrylate) Tetrahedron Lett 1972 1359 1362
29. G.A. Di Marzo, and F. Dowell Theoretical prediction of the specific heat of polymer glasses J Appl Phys 50 1979 6061 6066 (Pubitemid 10476046)
30. M. Gouterman Study of the effects of substitution on the absorption spectra of porphin J Chem Phys 30 1959 1139 1161
31. A.H. Corwin, A.B. Chivvis, R.W. Poor, D.G. Whitten, and E.W. Baker Porphyrin studies. XXXVII. The interpretation of porphyrin and metalloporphyrin spectra J Am Chem Soc 90 1968 6577 6583
32. M.S. Liao, and S. Scheiner Electronic structure and bonding in metal porphyrins, metal = Fe, Co, Ni, Cu, Zn J Chem Phys 117 2002 205 219 (Pubitemid 34789527)
33. R. Wang, and B.M. Hoffman Systematic trends in metalloporphyrin optical spectra J Am Chem Soc 106 1984 4235 4240
34. J.A. Shelnutt, and V. Ortiz Substituent effects on the electronic structure of metalloporphyrins: a quantitative analysis in terms of four-orbital-model parameters J Phys Chem 89 1985 4733 4739
35. C.A. Hunter, and J.K. Sanders The nature of π-π interactions J Am Chem Soc 112 1990 5525 5534
36. P.A.J. de Witte, M. Castriciano, J.J.L.M. Cornelissen, L. Monsù Scoalro, R.J.M. Nolte, and A.E. Rowan Helical polymer-anchored porphyrin nanorods Chem Eur J 9 2003 1775 1781
37. R. van Hameren, A.M. van Buul, M.A. Castriciano, N. Micali, P. Schön, and S. Speller et al. Supramolecular porphyrin polymers in solution and at the solid-liquid interface Nano Lett 8 2008 253 259 (Pubitemid 351177810)
38. S. Matile, N. Berova, K. Nakanishi, J. Fleischhauer, and R.W. Woody Structural studies by exciton coupled circular dichroism over a large distance: porphyrin derivatives of steroids, dimeric steroids, and brevetoxin B J Am Chem Soc 118 1996 5198 5206 (Pubitemid 26201540)