Large-Scale Synthesis of Helicene-Like Molecules for the Design of Enantiopure Thin Films with Strong Chiroptical Activity

被引:23
作者
Bensalah-Ledoux, Amina [5 ]
Pitrat, Delphine [1 ]
Reynaldo, Thibault [2 ]
Srebro-Hooper, Monika [3 ]
Moore, Barry, II [4 ]
Autschbach, Jochen [4 ]
Crassous, Jeanne [2 ]
Guy, Stephan [5 ]
Guy, Laure [1 ]
机构
[1] Univ Lyon, CNRS, Ecole Normale Super Lyon, Chim Lab,UMR 5182, 46 Allee Italie, F-69364 Lyon 07, France
[2] Univ Rennes, CNRS, Inst Sci Chim Rennes, UMR 6226, Campus Beaulieu, F-135042 Rennes, France
[3] Jagiellonian Univ, Fac Chem, Dept Theoret Chem, R Ingardena 3, PL-30060 Krakow, Poland
[4] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
[5] Univ Lyon 1, CNRS, Inst Lumiere Mat, UMR5306, F-69622 Villeurbanne, France
基金
美国国家科学基金会;
关键词
chiroptical properties; circular dichroism; dibenzo[c]acridine derivatives; helicenes; thin films; VIBRATIONAL CIRCULAR-DICHROISM; DENSITY-FUNCTIONAL THEORY; ABSOLUTE-CONFIGURATION; POLARIZED LUMINESCENCE; RESOLUTION; QUINOLINES; EFFICIENT; DERIVATIVES; ACCESS; SALT;
D O I
10.1002/chem.201504174
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Helicenes are fascinating molecules owing to their unusual properties and applications in many fields from catalysis to organic electronics. Herein, we report a straightforward pathway for the synthesis of helicene-like molecules on a gram scale in an enantiopure form. Thin-film materials with good propagating optical properties and very high chiroptical responses have been grown by using pulsed laser ablation without altering the structure or the enantiopurity of the molecules. Moreover, electronic and vibrational circular dichroism spectroscopies coupled with theoretical calculations enabled some dependences of the chiroptical properties with the structure to be highlighted, for example, effects of rigidification, aromatization, or the state of matter (liquid versus solid).
引用
收藏
页码:3333 / 3346
页数:14
相关论文
共 62 条
[1]   Helical Sense-Responsive and Substituent-Sensitive Features in Vibrational and Electronic Circular Dichroism, in Circularly Polarized Luminescence, and in Raman Spectra of Some Simple Optically Active Hexahelicenes [J].
Abbate, Sergio ;
Longhi, Giovanna ;
Lebon, France ;
Castiglioni, Ettore ;
Superchi, Stefano ;
Pisani, Laura ;
Fontana, Francesca ;
Torricelli, Franck ;
Caronna, Tullio ;
Villani, Claudio ;
Sabia, Rocchina ;
Tommasini, Matteo ;
Lucotti, Andrea ;
Mendola, Daniele ;
Mele, Andrea ;
Lightner, David A. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2014, 118 (03) :1682-1695
[2]   Experimental and calculated vibrational and electronic circular dichroism spectra of 2-Br-hexahelicene [J].
Abbate, Sergio ;
Lebon, France ;
Longhi, Giovanna ;
Fontana, Francesca ;
Caronna, Tullio ;
Lightner, David A. .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2009, 11 (40) :9039-9043
[3]   Ruthenium-Vinylhelicenes: Remote Metal-Based Enhancement and Redox Switching of the Chiroptical Properties of a Helicene Core [J].
Anger, Emmanuel ;
Srebro, Monika ;
Vanthuyne, Nicolas ;
Toupet, Loic ;
Rigaut, Stephane ;
Roussel, Christian ;
Autschbach, Jochen ;
Crassous, Jeanne ;
Reau, Regis .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (38) :15628-15631
[4]   From Hetero- to Homochiral Bis(metallahelicene)s Based on a PtIII-PtIII Bonded Scaffold: Isomerization, Structure, and Chiroptical Properties [J].
Anger, Emmanuel ;
Rudolph, Mark ;
Shen, Chengshuo ;
Vanthuyne, Nicolas ;
Toupet, Loic ;
Roussel, Christian ;
Autschbach, Jochen ;
Crassous, Jeanne ;
Reau, Regis .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (11) :3800-3803
[5]  
[Anonymous], 2003, ANGEW CHEM, V115, P3270
[6]  
[Anonymous], 2012, Comprehensive Chiroptical Spectroscopy
[7]  
[Anonymous], 2013, ANGEW CHEM, V125, P1840
[8]  
[Anonymous], 2010, ANGEW CHEM, V122, P103
[9]   Delocalization Error and "Functional Tuning" in Kohn-Sham Calculations of Molecular Properties [J].
Autschbach, Jochen ;
Srebro, Monika .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (08) :2592-2602
[10]   Time-Dependent Density Functional Response Theory for Electronic Chiroptical Properties of Chiral Molecules [J].
Autschbach, Jochen ;
Nitsch-Velasquez, Lucia ;
Rudolph, Mark .
ELECTRONIC AND MAGNETIC PROPERTIES OF CHIRAL MOLECULES AND SUPRAMOLECULAR ARCHITECTURES, 2011, 298 :1-98