Chiral Optical Properties of Phenyloxazoline Derivatives that Appear Only in the Solid State

Unlike in the solution state, the circularly polarized luminescence (CPL) of the chiral oxazoline compound 4-(4-isopropyl-4,5-dihydrooxazol-2-yl)benzonitrile, having one oxazoline unit, was observed in the solid state. On the other hand, although the CPL of the chiral oxazoline compound 1,4-bis(4-isopropyl-4,5-dihydrooxazol-2-yl)benzene, having two oxazoline units, was not observed, its circular dichroism (CD) property changed significantly according to the state (i.e., solution or solid state).

[1]  G. Konishi,et al.  Polymer-Chain-Induced Tunable Luminescence Properties: Amphiphilic Poly(2-oxazoline)s Possessing a N,N-Dialkylpyrene-1-carboxamide Chromophore in the Side Chain , 2012 .

[2]  Tomohiro Sato,et al.  Nonclassical tunability of solid-state CD and CPL properties of a chiral 2-naphthalenecarboxylic acid/amine supramolecular organic fluorophore. , 2012, Chemistry, an Asian journal.

[3]  Tomohiro Sato,et al.  Chiral supramolecular thiophene fluorophore consisting of thiophenecarboxylic acid derivatives , 2011 .

[4]  T. Kawai,et al.  Noncovalent ligand-to-ligand interactions alter sense of optical chirality in luminescent tris(β-diketonate) lanthanide(III) complexes containing a chiral bis(oxazolinyl) pyridine ligand. , 2011, Journal of the American Chemical Society.

[5]  Tomohiro Sato,et al.  Control of the solid-state chiral optical properties of a supramolecular organic fluorophore containing 4-(2-arylethynyl)-benzoic acid. , 2011, Chemistry, an Asian journal.

[6]  E. Vasile,et al.  Oxazoline-functional polymer particles graft with azo-dye , 2011 .

[7]  Tsuyoshi Kawai,et al.  Circularly Polarized Light from Chiral Lanthanide(III) Complexes in Single Crystals , 2011 .

[8]  J. Pécaut,et al.  Diastereoselective self-assembly of a homochiral europium triangle from a bipyoxazoline-carboxylate ligand. , 2010, Chemistry.

[9]  Tomohiro Sato,et al.  Control of solid-state chiral optical properties of a chiral supramolecular organic fluorophore consisting of 1-pyrenesulfonic acid and chiral amine molecules , 2010 .

[10]  Kenji Matsumoto,et al.  A chiral 2,6-bis(oxazolinyl)pyridine ligand with amide groups to form isomorphous complexes through all the lanthanoid series. , 2010, Inorganic chemistry.

[11]  Jiu-Haw Lee,et al.  Emission Characteristics of Organic Light-Emitting Diodes and Organic Thin-Films with Planar and Corrugated Structures , 2010, International journal of molecular sciences.

[12]  Tomohiro Sato,et al.  A 2D Layered Chiral Supramolecular Organic Fluorophore Composed of 1‐Amino‐2‐indanol and Carboxylic Acid Derivatives , 2010 .

[13]  P. Sonar,et al.  Cubic silsesquioxanes for use in solution processable organic light emitting diodes (OLED) , 2009 .

[14]  Chongwu Zhou,et al.  Wafer-scale fabrication of separated carbon nanotube thin-film transistors for display applications. , 2009, Nano letters.

[15]  Jang‐Joo Kim,et al.  Excitation energy transfer in organic materials: from fundamentals to optoelectronic devices. , 2009, Macromolecular rapid communications.

[16]  Cheuk‐Lam Ho,et al.  Functional metallophosphors for effective charge carrier injection/transport: New robust OLED materials with emerging applications , 2009 .

[17]  Tomohiro Sato,et al.  Complexation Behavior of a Supramolecular Organic Fluorophore Prepared by Solid‐State Co‐Grinding Crystallization Using 2‐Anthracenecarboxylic Acid and (R)‐1‐(2‐Naphthyl)ethylamine and Its Optical Properties , 2009 .

[18]  F. Diederich,et al.  Acetylene-derived strong organic acceptors for planar and nonplanar push-pull chromophores. , 2009, Accounts of chemical research.

[19]  S. Jie,et al.  Modular synthesis of oxazolines and their derivatives. , 2009, Journal of combinatorial chemistry.

[20]  Tomohiro Sato,et al.  Preparation of a spontaneous resolution chiral fluorescent system using 2-anthracenecarboxylic acid. , 2008, Organic & biomolecular chemistry.

[21]  E. List,et al.  Phosphorescent Organic Light-Emitting Devices: Working Principle and Iridium Based Emitter Materials , 2008, International journal of molecular sciences.

[22]  Y. Ooyama,et al.  Heterocyclic Quinol‐Type Fluorophores: Solid‐State Fluorescence Change in Crystals of Benzo[b]naphtho[1,2‐d]furan‐6‐one‐Type Fluorophore upon Inclusion of Organic Solvent Molecules , 2008 .

[23]  O. Reiser,et al.  Metal-bis(oxazoline) complexes: From coordination chemistry to asymmetric catalysis , 2008 .

[24]  T. Kawai,et al.  Enhanced deep-red luminescence of tris(hexafluoroacetylacetonato)samarium(III) complex with phenanthroline in solution by control of ligand coordination. , 2008, The journal of physical chemistry. A.

[25]  Subha Viswanathan,et al.  Thiophene-derivatized pybox and its highly luminescent lanthanide ion complexes. , 2007, Journal of the American Chemical Society.

[26]  J. Mayoral,et al.  QM/MM modeling of enantioselective pybox-ruthenium- and box-copper-catalyzed cyclopropanation reactions: scope, performance, and applications to ligand design. , 2007, Chemistry.

[27]  Tomohiro Sato,et al.  Solid-state optical properties of a chiral supramolecular fluorophore consisting of chiral (1R,2R)-1,2-diphenylethylenediamine and fluorescent carboxylic acid derivatives , 2007 .

[28]  Toshihiko Nagamura,et al.  Enhanced lasing properties of dissymmetric Eu(III) complex with bidentate phosphine ligands. , 2007, The journal of physical chemistry. A.

[29]  J. Bünzli,et al.  Dimeric Complexes of Lanthanide(III) Hexafluoroacetylacetonates with4‐Cyanopyridine N‐Oxide: Synthesis, Crystal Structure, Magnetic and Photoluminescent Properties , 2006 .

[30]  Y. Ooyama,et al.  Heterocyclic quinol-type fluorophores: synthesis, X-ray crystal structures, and solid-state photophysical properties of novel 5-hydroxy-5-substituent-benzo[b]naphtho[1,2-d]furan-6-one and 3-hydroxy-3-substituent-benzo[kl]xanthen-2-one derivatives. , 2006, Chemistry.

[31]  J. Tomasi,et al.  Quantum mechanical continuum solvation models. , 2005, Chemical reviews.

[32]  M. Albrecht,et al.  Anthryl-substituted heterocycles as acid-sensitive fluorescence probes. , 2005, The Journal of organic chemistry.

[33]  Chin‐Ti Chen,et al.  Derivative of α, β-dicyanostilbene: Convenient precursor for the synthesis of diphenylmaleimide compounds, E-Z isomerization, crystal structure, and solid-state fluorescence , 2004 .

[34]  D. Avnir,et al.  Quantitative chirality analysis of molecular subunits of bis(oxazoline)copper(II) complexes in relation to their enantioselective catalytic activity. , 2003, Chemistry.

[35]  P. Renaud,et al.  Chiral relay: a novel strategy for the control and amplification of enantioselectivity in chiral Lewis acid promoted reactions. , 2003, Chemistry.

[36]  Y. Ooyama,et al.  Heterocyclic quinol-type fluorophores. Part 1. Synthesis of new benzofurano[3,2-b]naphthoquinol derivatives and their photophysical properties in solution and in the crystalline state , 2002 .

[37]  P. Renaud,et al.  Chiral relay effect: 4-substituted 1,3-benzoxazol-2-(3H)-ones as achiral templates for enantioselective Diels-Alder reactions. , 2002, Organic letters.

[38]  Heinz Langhals,et al.  Persistent Fluorescence of Perylene Dyes by Steric Inhibition of Aggregation , 2000 .

[39]  J. S. Johnson,et al.  Chiral bis(oxazoline) copper(II) complexes: versatile catalysts for enantioselective cycloaddition, Aldol, Michael, and carbonyl ene reactions. , 2000, Accounts of chemical research.

[40]  Y. Wada,et al.  Enhanced Emission of Deuterated Tris(hexafluoroacetylacetonato)neodymium(III) Complex in Solution by Suppression of Radiationless Transition via Vibrational Excitation , 1996 .

[41]  Tatsuhiko Yamanaka,et al.  Enhancement of luminescence of Nd3+ complexes with deuterated hexafluoroacetylacetonato ligands in organic solvent , 1996 .

[42]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[43]  H. Langhals,et al.  Der Einfluß von Packungseffekten auf die Feststoffluoreszenz von Diketopyrrolopyrrolen , 1989 .

[44]  T. H. Dunning.  Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen , 1989 .

[45]  R. Kuroda,et al.  Solid-State Circular Dichroism Spectra of Tris(diamine)cobalt(III) Complexes: Decomposition into E and A2 Components , 1976 .

[46]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[47]  J. Bünzli,et al.  Fluorinated β-Diketones for the Extraction of Lanthanide Ions: Photophysical Properties and Hydration Numbers of Their EuIII Complexes , 2006 .

[48]  Joseph Shinar,et al.  Organic Light-Emitting Devices , 2004 .

[49]  George M. Sheldrick,et al.  SADABS, Program for Empirical Absorption Correction of Area Detector Data , 1996 .