Modulation of circularly polarized luminescence through excited-state symmetry breaking and interbranched exciton coupling in helical push-pull organic systems

被引:83
作者
Dhbaibi, Kais [1 ,8 ]
Favereau, Ludovic [1 ]
Srebro-Hooper, Monika [2 ]
Quinton, Cassandre [1 ]
Vanthuyne, Nicolas [3 ]
Arrico, Lorenzo [4 ]
Roisnel, Thierry [1 ]
Jamoussi, Bassem [5 ]
Poriel, Cyril [1 ]
Cabanetos, Clement [6 ]
Autschbach, Jochen [7 ]
Crassous, Jeanne [1 ]
机构
[1] Univ Rennes, CNRS, UMR 6226, ISCR,ScanMAT,UMS 2001, F-35000 Rennes, France
[2] Jagiellonian Univ, Fac Chem, Gronostajowa 2, PL-30387 Krakow, Poland
[3] Aix Marseille Univ, CNRS, Cent Marseille, ISm2, Marseille, France
[4] Univ Pisa, Dipartimento Chim & Chim Ind, Via Moruzzi 13, I-56124 Pisa, Italy
[5] King Abdulaziz Univ, Fac Meteorol Environm & Arid Land Agr, Dept Environm Sci, Jeddah 21589, Saudi Arabia
[6] Univ Angers, CNRS, UMR 6200, MOLTECH Anjou, 2 Bd Lavoisier, F-49045 Angers, France
[7] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
[8] Univ Gabes, Fac Sci Gabes, Zrig 6072, Gabes, Tunisia
基金
美国国家科学基金会;
关键词
CHARGE-TRANSFER; ENANTIOSELECTIVE SYNTHESIS; PHOTOPHYSICAL PROPERTIES; CHIROPTICAL PROPERTIES; DICHROISM; ELECTROLUMINESCENCE; 1,8-NAPHTHALIMIDE; MOLECULES; EFFICIENT; DESIGN;
D O I
10.1039/c9sc05231c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
pi-Helical push-pull dyes were prepared and their (chir)optical properties were investigated both experimentally and computationally. Specific fluorescent behaviour of bis-substituted system was observed with unprecedented solvent effect on the intensity of circularly polarized luminescence (CPL, dissymmetry factor decreasing from 10(-2) to 10(-3) with an increase in solvent polarity) that was linked to a change in symmetry of chiral excited state and suppression of interbranched exciton coupling. The results highlight the potential of CPL spectroscopy to study and provide a deeper understanding of electronic photophysical processes in chiral pi-conjugated molecules.
引用
收藏
页码:567 / 576
页数:10
相关论文
共 67 条
[1]  
Amabilino D. B., 2009, Chirality at the Nanoscale: Nanoparticles, Surfaces, Materials and More
[2]   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
[3]   Tuning symmetry breaking charge separation in perylene bichromophores by conformational control [J].
Aster, Alexander ;
Licari, Giuseppe ;
Zinna, Francesco ;
Brun, Elodie ;
Kumpulainen, Tatu ;
Tajkhorshid, Emad ;
Lacour, Jerome ;
Vauthey, Eric .
CHEMICAL SCIENCE, 2019, 10 (45) :10629-10639
[4]   Computing Chiroptical Properties with First-Principles Theoretical Methods: Background and Illustrative Examples [J].
Autschbach, Jochen .
CHIRALITY, 2009, 21 (1E) :E116-E152
[5]   Helicenes Grafted with 1,1,4,4-Tetracyanobutadiene Moieties: π-Helical Push-Pull Systems with Strong Electronic Circular Dichroism and Two-Photon Absorption [J].
Bouvier, Romain ;
Durand, Raphael ;
Favereau, Ludovic ;
Srebro-Hooper, Monika ;
Dorcet, Vincent ;
Roisnel, Thierry ;
Vanthuyne, Nicolas ;
Vesga, Yuly ;
Donnelly, Julie ;
Hernandez, Florencio ;
Autschbach, Jochen ;
Trolez, Yann ;
Crassous, Jeanne .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (54) :14484-14494
[6]   Circularly Polarized Phosphorescent Electroluminescence with a High Dissymmetry Factor from PHOLEDs Based on a Platinahelicene [J].
Brandt, Jochen R. ;
Wang, Xuhua ;
Yang, Ying ;
Campbell, Alasdair J. ;
Fuchter, Matthew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (31) :9743-9746
[7]   Recent Theoretical and Experimental Progress in Circularly Polarized Luminescence of Small Organic Molecules [J].
Chen, Naibo ;
Yan, Bo .
MOLECULES, 2018, 23 (12)
[8]  
Chen Y. S. C.-F., 2017, HELICENES CHEM SYNTH
[9]   Excited-State Symmetry Breaking in a Quadrupolar Molecule Visualized in Time and Space [J].
Dereka, Bogdan ;
Rosspeintner, Arnulf ;
Stezycki, Rafal ;
Ruckebusch, Cyril ;
Gryko, Daniel T. ;
Vauthey, Eric .
JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2017, 8 (24) :6029-6034
[10]   Solute-Solvent Interactions and Excited-State Symmetry Breaking: Beyond the Dipole-Dipole and the Hydrogen-Bond Interactions [J].
Dereka, Bogdan ;
Vauthey, Eric .
JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2017, 8 (16) :3927-3932