N. Barbero et al. / Dyes and Pigments 92 (2012) 1177e1183
1183
electroluminescent emitters and nonlinear optical materials. J Phys Chem
2010;114:11602e6.
[4] Nalwa HS, Miyata S, editors. Nonlinear optics of organic molecules and
polymers. Boca Raton, FL: CRC Press; 1997.
[5] Fiorilli S, Onida B, Barolo C, Viscardi G, Brunel D, Garrone E. Tethering of
modified Reichardt’s dye on SBA-15 mesoporous silica: the effect of the linker
flexibility. Langmuir 2007;23:2261e8.
[6] Zu LL, Li X, Ji FY, Ma X, Wang QC, Tian H. Photolockable ratiometric viscosity
sensitivity of cyclodextrin polypseudorotaxane with light-active rotor graft.
Langmuir 2009;25:3482e6.
[24] Castelino RW, Hallas G. Electronic absorption spectra of some julolidine
(2,3,6,7-tetrahydro-1H, 5H-benzo[ij]quinolizine) analogues of 4-dimethyl
aminoazobenzenes. J Chem Soc B Phys Org 1971;5:793e5.
[25] Hallas G. Proton magnetic resonance spectra of some para-substituted
derivatives of 9-phenylazojulolidine (9-phenylazo-2,3,6,7-tetrahydro-1H,5H-
benzo[ij]quinolizine). J Chem Soc C Org 1971;17:2847e8.
[26] Hallas G, Saadatjou N, Hepworth JD, Ibbitson DA, Jones AM, Keane TP, et al.
Dipole moments of derivatives of 4-phenylazo-NN-diethylaniline and of
9-phenylazojulolidine (9-phenylazo-2,3,6,7-tetrahydro-1H,5H-benzo[ij]qui-
nolizine). J Chem Soc. Perkin Trans 1981;2(9):1292e4.
[7] Quagliotto P, Barbero N, Barolo C, Costabello K, Marchese L, Coluccia S, et al.
Characterization of monomeric and gemini cationic amphiphilic molecules by
fluorescence intensity and anisotropy. Dyes Pigments 2009;82:124e9.
[8] Barbero N, Quagliotto P, Barolo C, Artuso E, Buscaino R, Viscardi G. Charac-
terization of monomeric and gemini cationic amphiphilic molecules by fluo-
rescence intensity and anisotropy. Part 2. Dyes Pigments 2009;83:396e402.
[9] Barbero N, Napione L, Quagliotto P, Pavan S, Barolo C, Barni E, et al. Fluores-
cence anisotropy analysis of protein-antibody interaction. Dyes Pigments
2009;83:225e9.
[10] Benzi C, Bertolino CA, Miletto I, Ponzio P, Barolo C, Viscardi G, et al. The design,
synthesis and characterization of a novel acceptor for real time polymerase
chain reaction using both computational and experimental approaches. Dyes
Pigments 2009;83:111e20.
[27] Zyss J, editor. Molecular nonlinear optics: materials, physics and devices.
Boston: Academic Press; 1994.
[28] Coe BJ, Foxon SP, Harper EC, Harris JA, Helliwell M, Raftery J, et al. The
syntheses, structures and nonlinear optical and related properties of salts
with julolidinyl electron donor groups. Dyes Pigments 2009;82:171e86.
[29] Sheldrick GM. SHELXTL, Version 5.1. Madison, WI: Bruker AXS Inc.; 1997.
[30] SMART, SAINT, SADABS, Xprep Software for CCD diffractometers. Madison,
WI: Bruker AXSInc.; 2003.
[31] Mori Y, Niwa T, Toyoshi K. Carcinogenic azo dyes. XVIII. Synthesis of azo dyes
related to 30-Hyroxy-methyl-4-(dimethylamino)azobenzene, a New Potent
Hepatocarcinogen. Chem Pharm Bull 1981;29:1439e42.
[32] Fisichella S. Azo-composti da p-amminobenzilalcool per acetilcellulosa
e
nylon. Tinctoria 1970;10:329e30.
[11] Barbero N, Barni E, Barolo C, Quagliotto P, Viscardi G, Napione L, et al. A study
of the interaction between fluorescein sodium salt and bovine serum albumin
by steady-state fluorescence. Dyes Pigments 2009;80:307e13.
[12] Barbero N, Napione L, Visentin S, Alvaro M, Veglio A, Bussolino F, et al.
A transient kinetic study between signaling proteins: the case of the MEK-ERK
interaction. Chem Sci 2011;2:1804e9.
[33] Toro C, Thibert A, De Boni L, Masunov AE, Hernández FE. Fluorescence
emission of Disperse Red 1 in solution at room temperature. J Phys Chem B
2008;112:929e37. and reference therein.
[34] Susdorf T, Bansal AK, Penzkofer A, Guo SL, Shi JM. Absorption and emission
spectroscopic characterization of some azo dyes and a diamino-maleonitrile
dye. Chem Phys 2007;333:49e56.
[13] Nazeeruddin MK, De Angelis F, Fantacci S, Selloni A, Viscardi G, Liska P, et al.
Combined experimental and DFT-TDDFT computational study of photo-
electrochemical cell ruthenium sensitizers. J Am Chem Soc 2005;127:16835e47.
[14] Buscaino R, Baiocchi C, Barolo C, Medana C, Grätzel M, Nazeeruddin MdK, et al.
A mass spectrometric analysis of sensitizer solution used for dye-sensitized
solar cell. Inorg Chim Acta 2008;361:798e805.
[35] Misra A, Shahid M, Srivastava P. An efficient fluoroionophore for selective
recognition of Hg2þ and Cu2þ ions. Thin Solid Films 2010;519:1235e9.
[36] Bouwstra JA, Schouten A, Kroon J. Structural studies of the system trans-
azobenzene/trans-stilbene. I. A reinvestigation of the disorder in the crystal
structure of trans-azobenzene, C12H10N2. Acta Crystallogr Sect C-Cryst Struct
Commun 1983;39:1121e3.
[15] Functional or “high technology” dyes and pigments. In: Christie RM, editor.
Colour chemistry. Cambridge: RSC; 2001. p. 168e90.
[37] Freeman HS, Posey JC, Singh J-P. X-ray crystal-structure of Disperse Red-167.
Dyes Pigments 1992;20:279e89.
[16] Yoshida Z, Shirota Y. Chemistry of functional dyes, vol. 2. Mita Press; 1993.
[17] Piron R, Brasselet S, Josse D, Zyss J, Viscardi G, Barolo C. Matching molecular
and optical multipoles in photoisomerizable nonlinear systems. J Opt Soc Am
B-Opt Phys 2005;22:1276e82.
[18] Ledoux I, Zyss J, Barni E, Barolo C, Diulgheroff N, Quagliotto P, et al. Properties
of novel azodyes containing powerful acceptor groups and thiophene moiety.
Synth Met 2000;115:213e7.
[19] Li Z, Wu W, Li Q, Yu G, Xiao L, Liu Y, et al. High-generation second-order
nonlinear optical (NLO) dendrimers: convenient synthesis by click chem-
istry and the increasing trend of NLO effects. Angew Chem Int Ed 2010;49:
2763e7.
[20] Li Z, Wang L, Xiong B, Ye C, Qin J, Li Z. Novel, side-on, PVK-based nonlinear
optical polymers: synthesis and NLO properties. Dyes Pigments 2010;84:
134e9.
[38] Park K-M, Yoon I, Lee SS, Choi G, Lee JS. X-ray crystal structure of CI Disperse
Blue 79. Dyes Pigments 2002;54:155e61.
[39] McIntosh SA, Freeman HS, Singh P. X-ray crystal-structure of the dye 4-(N,
N-bis-(beta-hydroxyethyl) amino) azobenzene. Dyes Pigments 1991;17:1e10.
[40] Le Page Y, Gabe EJ, Wang J, Barclay LRC, Holm HL. 2,20,4,40,6,60-Hexa-tert-
butylazobenzene. Acta Crystallogr Sect B-Struct Sci 1980;36:2846e8.
[41] Lee J-E, Kim HJ, Han MR, Lee SY, Jo WJ, Lee SS, et al. Crystal structures of C.I.
Disperse Red 65 and C.I. Disperse Red 73. Dyes Pigments 2009;80:181e6.
[42] Le Page Y, Gabe EJ, Barclay LRC, Dust JM. 2,20,4,40,6,60-Hexaisopropylazobenzene.
Acta Crystallogr Sect B-Struct Sci 1981;37:976e8.
[43] Harada J, Ogawa K, Tomoda S. Molecular motion and conformational inter-
conversion of azobenzenes in crystals as studied by X-ray diffraction. Acta
Crystallogr Sect B-Struct Sci 1997;53:662e72.
[44] Desiraju GR, Steiner T. The weak hydrogen bond in structural chemistry and
biology. Oxford University Press; 1999.
[21] Zeng Q, Qiu G, Ye C, Qin J, Li Z. New second-order nonlinear optical poly-
phosphazenes: convenient postfunctionalization synthetic approach and
application of the concept of suitable isolation group. Dyes Pigments 2010;84:
229e36.
[45] Argay G, Sasvári K. The crystal and molecular structure of azobisisobutyr-
onitrile, C8H12N4. Acta Crystallogr Sect B-Struct Sci 1971;27:1851e8.
[46] Bindu P, Varghese B, Rao MNS. Six coordinate tris(catecholato)silicates of
primary amine residues-synthesis, characterization, and thermolysis studies.
X-ray structures of [n-C3H7NH3](2)[Si(C6H4O2)3]center dot 1/2(C6H14N2) and
ꢀ
[22] Seferoglu Z, Ertan N, Kickelbick G, Hökelek T. Single crystal X-ray structure
analysis for two thiazolylazo indole dyes. Dyes Pigments 2009;82:20e5.
[23] Hepworth JD, Mason D, Hallas G, Marsden R. The effects of cyclic terminal
groups in 4-aminoazobenzene and related azo dyes. 2. -Pka values of some
monoazo dyes derived from N-phenylpyrrolidine and N-phenylpiperidine.
Dyes Pigments 1985;6:389e96.
of
a bulky secondary ammonium ion, [(i-C4H9)(2)NH2](2)[Si(C6H4O2)(3)]
center dot H2O. Phosphorus Sulfur Silicon Relat Elem 2003;178:2373e6.
[47] Gabe EJ, Wang Y, Barclay LRC, Holm HL. 2, 20, 4, 40, 6, 60-Hexamethylazo-
benzene. Acta Crystallogr Sect B-Struct Sci 1981;37:978e9.