The synthesis of novel, unsymmetrically substituted, chiral naphthalene and perylene diimides: Photophysical, electrochemical, chiroptical and intramolecular charge transfer properties

Dyes and Pigments

Volumn 84, Issue 1, 2010, Pages 1-13

  Asir, Suleyman ^a   Demir, Ayhan S ^b   Icil, Huriye ^a  

^a EASTERN MEDITERRANEAN UNIVERSITY   (Turkey)

^b MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Charge transfer; Chirality; Cyclic voltammetry; Exciplex; Unsymmetrical naphthalene diimides; Unsymmetrical perylene diimides

Indexed keywords

APROTIC SOLVENTS; COTTON EFFECTS; DIIMIDE; EXCIMER-LIKE EMISSION; EXCIPLEX; INTRA-MOLECULAR CHARGE TRANSFER; NAPHTHALENE DIIMIDE; NON-POLAR; PERYLENE DIIMIDES; PERYLENES; PHOTOPHYSICAL; POLAR SOLVENTS; UNSYMMETRICAL; UNSYMMETRICAL NAPHTHALENE DIIMIDES; UNSYMMETRICAL PERYLENE DIIMIDES;

CHARGE TRANSFER; CHIRALITY; CYCLIC VOLTAMMETRY; ELECTROCHEMICAL PROPERTIES; ELECTRON TRANSITIONS; ENANTIOMERS; ION EXCHANGE; MASS TRANSFER; OPTICAL ROTATION; STEEL BEAMS AND GIRDERS; STEREOCHEMISTRY; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

NAPHTHALENE;

CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; COTTON; ORGANIC COMPOUND; SOLVENT; SYNTHESIS;

EID: 69349091005     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.04.014     Document Type: Article

References (56)

1. Todd E.K., Wang S., Wan X., and Wang Z.Y. Chiral imides as potential chiroptical switches: synthesis and optical properties. Tetrahedron Letters 46 (2005) 587-590
2. Zhou Y., Zhang D., Zhang Y., Tang Y., and Zhu D.J. Tuning the CD spectrum and optical rotation value of a new binaphthalene molecule with two spiropyran units: mimicking the function of a molecular "AND" logic gate and a new chiral molecular switch. Journal of Organic Chemistry 70 (2005) 6164-6170
3. Zhang J., Albelda M.T., Liu Y., and Canary J.W. Chiral nanotechnology. Chirality 17 (2005) 404-420
4. Uzun D., Ozser M.E., Yuney K., Icil H., and Demuth M.J. Synthesis and photophysical properties of N, N′-bis(4-cyanophenyl)-3,4,9,10-perylenebis(dicarboximide) and N, N′-bis(4-cyanophenyl)-1,4,5,8-naphthalenediimide. Journal of Photochemistry and Photobiology A - Chemistry 156 (2003) 45-54
5. Dou Z., Li X., Zhong S., Zhao C., and Na H. The synthesis and characterization of a novel ternary polymer bisphenol A-4,4′-difluorobenzophenone-bis(p-hydroxyphenyl)-1,4,5,8-naphthale netetracarboxylic diimide monomer. Polymer Bulletin 57 (2006) 351-358
6. Figueiredo K.M., Marcon R.O., Campos I.B., Nantes I.L., and Brochsztain S. Photoinduced electron transfer between cytochrome c and a novel 1,4,5,8-naphthalenetetracarboxylic diimide with amphiphilic character. Journal of Photochemistry and Photobiology B - Biology 79 (2005) 1-9
7. Nagao Y. Synthesis and properties of perylene pigments. Progress in Organic Coatings 31 (1997) 43-49
8. Shchepinov M.S., Korshun V.A., Egeland R.D., and Southern E.M. Tritylisation of pyrene, perylene and coronene: a new family of switchable fluorescent labels. Tetrahedron Letters 41 (2000) 4943-4948
9. Langhals H., Ismael R., and Yürük O. Persistent fluorescence of perylene dyes by steric inhibition of aggregation. Tetrahedron 56 (2000) 5435-5441
10. Tomizaki K., Loewe R.S., Kirmaier C., Schwartz J.K., Retsek J.L., Bocian D.F., et al. Of light-harvesting arrays comprised of a porphyrin bearing multiple perylene-monoimide accessory pigments. Journal of Organic Chemistry 67 (2002) 6519-6534
11. Pasaogullari N., Icil H., and Demuth M. Symmetrical and unsymmetrical perylene diimides: their synthesis, photophysical and electrochemical properties. Dyes and Pigments 69 (2006) 118-127
12. Baffreau J., Leroy-Lhez S., Anh N.V., Williams R.M., and Hudhomme P. Fullerene c60-perylene-3,4:9,10-bis(dicarboximide) light-harvesting dyads: spacer-length and bay-substituent effects on intramolecular singlet and triplet energy transfer. Chemistry A European Journal 14 (2008) 4974-4992
13. Hippius C., vanStokkum I.H.M., Gsänger M., Groeneveld M.M., Williams R.M., and Würthner F. Sequential FRET processes in calix[4]arene-linked orange-red-green perylene bisimide dye zigzag arrays. Journal of Physical Chemistry C 112 (2008) 2476-2486
14. Veldman D., Chopin S.M.A., Meskers S.C.J., Groeneveld M.M., Williams R.M., and Janssen R.A.J. Triplet formation involving a polar transition state in a well-defined intramolecular perylenediimide dimeric aggregate. Journal of Physical Chemistry A 112 (2008) 5846-5857
15. Gawroński J., Brzostowska M., Kacprzak K., Kołbon H., and Skowronek P. Chirality of aromatic bis-imides from their circular dichroism spectra. Chirality 12 (2000) 263-268
16. Sterzel M., Pilch M., Pawlikowski M.T., and Gawroński J. The circular dichroism (CD) and absorption studies of 1,4,5,8-naphthalene tetracarboxydiimide dimer in terms of vibronic coupling theory. Chemical Physics 291 (2003) 251-260
17. Langhals H., and Gold J. Chiral bifluorophoric perylene dyes with unusually high CD effects -- a simple model for the photosynthesis reaction center. Liebigs Annalen 1997 (1997) 1151-1153
18. Langhals H., and Krotz O. Chiral, bichromophoric silicones: ordering principles of structural units in complex molecules. Angewandte Chemie International Edition 45 (2006) 4444-4447
19. Sun R., Xue C., Owak M., Peetz R.M., and Jin S. Facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides involving α-amino acids. Tetrahedron Letters 48 (2007) 6696-6699
20. Zheng J., Qiao W., Wan X., Ping Gao J., and Wang Z.Y. Near-infrared electrochromic and chiroptical switching materials: design, synthesis, and characterization of chiral organogels containing stacked naphthalene diimide chromophores. Chemistry of Materials 20 (2008) 6163-6168
21. Amiralaei S., Uzun D., and İcil H. Chiral substituent containing perylene monoanhydride monoimide and its highly soluble symmetrical diimide: synthesis, photophysics and electrochemistry from dilute solution to solid state. Photochemical and Photobiological Sciences 7 (2008) 936-947
22. Osswald P., Reichert M., Bringmann G., and Würthner F. Perylene bisimide atropisomers: synthesis, resolution, and stereochemical assignment. Journal of Organic Chemistry 72 (2007) 3403-3411
23. Xue C., Chen M., and Jin S. Synthesis and characterization of the first soluble nonracemic chiral main-chain perylene tetracarboxylic diimide polymers. Polymer 49 (2008) 5314-5321
24. Dehm V., Chen Z., Baumeister U., Prins P., Siebbeles L.D.A., and Würthner F. Helical growth of semiconducting columnar dye assemblies based on chiral perylene bisimides. Organic Letters 9 (2007) 1085-1088
25. Tröster H. Untersuchungen zur Protonierung von Perylen-3,4,9,10-tetracarbonsäurealkalisalzen. Dyes and Pigments 4 (1983) 171-177
26. Hopkins H.P., Stevenson K.A., and Wilson W.D. Enthalpy and entropy changes for the intercalation of small molecules to DNA.I. Substituted naphthalene monoimides and naphthalene diimides. Journal of Solution Chemistry 15 (1986) 563-579
27. Lokey R.S., Kwok Y., Guelev V., Pursell C.J., Hurley L.H., and Iverson B.L. A new class of polyintercalating molecules. Journal of the American Chemical Society 119 (1997) 7202-7210
28. Gianolio D.A., Segismundo J.M., and McLaughlin L.W. Tethered naphthalene diimide-based intercalators for DNA triplex stabilization. Nucleic Acids Research 28 (2000) 2128-2134
29. Asseline U., and Cheng E. Synthesis and binding properties of perylene-oligo-2′-deoxyribonucleotide conjugates. Tetrahedron Letters 42 (2001) 9005-9010
30. Rahe N., Rinn C., and Carell T. Development of donor-acceptor modified DNA hairpins for the investigation of charge hopping kinetics in DNA. Chemical Communications 17 (2003) 2120-2121
31. Lewis F.D., Zhang L., Kelley R.F., McCamant D., and Wasielewski M.R. A perylenedicarboxamide linker for DNA hairpins. Tetrahedron 63 (2007) 3457-3464
32. Haga M., Ohta M., Machida H., Chikira M., and Tonegawa N. Point-to-point capture of DNA with the aid of intercalation by immobilized rod-shaped Ru complexes at solid surface towards nanowiring. Thin Solid Films 499 (2006) 201-206
33. Zandonella G., Haalck L., Spener F., Faber K., Paltauf F., and Hermetter A. Enantiomeric perylene-glycerolipids as fluorogenic substrates for a dual wavelength assay of lipase activity and stereoselectivity. Chirality 8 (1996) 481-489
34. Horne W.S., Ashkenasy N., and Ghadiri M.R. Modulating charge transfer through cyclic d, l α-peptide self-assembly. Chemistry 11 (2005) 1137-1144
35. Ashkenasy N., Horne W.S., and Ghadiri M.R. Design of self-assembling peptide nanotubes with delocalized electronic states. Small 2 (2006) 99-102
36. Thalacker C., and Würthner F. Chiral perylene bisimide-melamine assemblies: hydrogen bond-directed growth of helically stacked dyes with chiroptical properties. Advanced Functional Materials 12 (2002) 209-218
37. Schenning A.P.H.J., Herrikhuyzen J., Jonkheijm P., Chen Z., Würthner F., and Meijer E.W. Photoinduced electron transfer in hydrogen-bonded oligo(p-phenylene vinylene)-perylene bisimide chiral assemblies. Journal of the American Chemical Society 124 (2002) 10252-10253
38. Herrikhuyzen J., Syamakumari A., Schenning A.P.H.J., and Meijer E.W. Synthesis of n-type perylene bisimide derivatives and their orthogonal self-assembly with p-type oligo(p-phenylene vinylene)s. Journal of the American Chemical Society 126 (2004) 10021-10027
39. Würthner F., Chen Z., Hoeben F.J.M., Osswald P., You C.C., Jonkheijm P., et al. Schoot PPAMvd, Meijer EW, Beckers EHA, Meskers SCJ, Janssen RAJ. Supramolecular p-n-heterojunctions by co-self-organization of oligo(p-phenylene vinylene) and perylene bisimide dyes. Journal of the American Chemical Society 126 (2004) 10611-10618
40. Masu H., Mizutani I., Kato T., Azumaya I., Yamaguchi K., Kishikawa K., et al. Foldamers with iminodicarbonyl linkers: their stabilities and application to a chiral photochromic system using retro [4 + 4] cycloaddition. Journal of Organic Chemistry 71 (2006) 8037-8044
41. Franke D., Vos M., Antonietti M., Sommerdijk N.A.J.M., and Faul C.F.J. Induced supramolecular chirality in nanostructured materials: ionic self-assembly of perylene-chiral surfactant complexes. Chemistry of Materials 18 (2006) 1839-1847
42. Lukas A.S., Miller S.E., and Wasielewski M.R. Femtosecond optical switching of electron transport direction in branched donor-acceptor arrays. Journal of Physical Chemistry B 104 (2000) 931-940
43. Andric G., Boas J.F., Bond A.M., Fallon G.D., Ghiggino K.P., Hogan C.F., et al. Spectroscopy of naphthalene diimides and their anion radicals. Australian Journal of Chemistry 57 (2004) 1011-1019
44. Wilson J.N., Gao J., and Kool E.T. Oligodeoxyfluorosides: strong sequence dependence of fluorescence emission. Tetrahedron 63 (2007) 3427-3433
45. Turro N.J. Molecular photochemistry (1965), Benjamin, Inc, New York, W.A. 4-48
46. Peng Z., Bao Z., and Galvin M.E. Polymers with bipolar carrier transport abilities for light emitting diodes. Chemistry of Materials 10 (1998) 2086-2090
47. Bredas J.L., Silbey R., Boudreaux D.S., and Chance R.R. Chain-length dependence of electronic and electrochemical properties of conjugated systems: polyacetylene, polyphenylene, polythiophene, and polypyrrole. Journal of the American Chemical Society 105 (1983) 6555-6559
48. Bard A.J., and Faulkner L.R. Electrochemical methods, fundamentals and applications (1980), Wiley & Sons Inc, New York
49. Kahlert H., Retter U., Lohse H., Siegler K., and Scholz F. On the determination of the diffusion coefficients of electrons and of potassium ions in copper(II) hexacyanoferrate(II) composite electrodes. Journal of Physical Chemistry B 102 (1998) 8757-8765
50. Lovric M., and Scholz F. A model for the coupled transport of ions and electrons in redox conductive microcrystals. Journal of Solid State Electrochemistry 3 (1999) 172-175
51. Lovric M., Hermes M., and Scholz F. Solid state electrochemical reactions in systems with miscibility gaps. Journal of Solid State Electrochemistry 4 (2000) 394-401
52. Schröder U., and Scholz F. The solid-state electrochemistry of metal octacyanomolybdates, octacyanotungstates, and hexacyanoferrates explained on the basis of dissolution and reprecipitation reactions, lattice structures, and crystallinities. Inorganic Chemistry 39 (2000) 1006-1015
53. Hermes M., Lovric M., Hartl M., Retter U., and Scholz F. On the electrochemically driven formation of bilayered systems of solid Prussian-blue-type metal hexacyanoferrates: a model for Prussian blue/cadmium hexacyanoferrate supported by finite difference simulations. Journal of Electroanalytical Chemistry 501 (2001) 193-204
54. Widmann A., Kahlert H., Petrovic-Prelevic I., Wulff H., Yakhmi J.V., Bagkar N., et al. Structure, insertion electrochemistry and magnetic properties of a new type of substitutional solid solutions of copper, nickel and iron hexacyanoferrates/hexacyanocobaltates. Inorganic Chemistry 41 (2002) 5706-5715
55. Grygar T., Marken F., Schröder U., and Scholz F. Electrochemical analysis of solids. Collection of Czechoslovak Chemical Communications 67 (2002) 163-208
56. Entire database of bibliography on the voltammetry of immobilized microparticles is available on: http://www.chemie.uni-greifswald.de/∼analytik/