Intermolecular London Dispersion Interactions of Azobenzene Switches for Tuning Molecular Solar Thermal Energy Storage Systems

被引:48
作者
Kunz, Anne [1 ,2 ]
Heindl, Andreas H. [1 ,2 ]
Dreos, Ambra [3 ]
Wang, Zhihang [3 ]
Moth-Poulsen, Kasper [3 ]
Becker, Jonathan [4 ]
Wegner, Hermann A. [1 ,2 ]
机构
[1] Justus Liebig Univ, Inst Organ Chem, Heinrich Buff Ring 17, D-35392 Giessen, Germany
[2] Justus Liebig Univ, Ctr Mat Res LaMa, Heinrich Buff Ring 16, D-35392 Giessen, Germany
[3] Chalmers Univ Technol, Dept Chem & Chem Engn, SE-41296 Gothenburg, Sweden
[4] Justus Liebig Univ, Inst Inorgan & Analyt Chem, Heinrich Buff Ring 17, D-35392 Giessen, Germany
关键词
azobenzene; London dispersions; thermal energy storage; molecular switches; noncovalent interactions; PHOTOSWITCHES; RELEASE;
D O I
10.1002/cplu.201900330
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The performance of molecular solar thermal energy storage systems (MOST) depends amongst others on the amount of energy stored. Azobenzenes have been investigated as high-potential materials for MOST applications. In the present study it could be shown that intermolecular attractive London dispersion interactions stabilize the (E)-isomer in bisazobenzene that is linked by different alkyl bridges. Differential scanning calorimetry (DSC) measurements revealed, that this interaction leads to an increased storage energy per azo-unit of more than 3 kcal/mol compared to the parent azobenzene. The origin of this effect has been supported by computation as well as X-ray analysis. In the solid state structure attractive London dispersion interactions between the C-H of the alkyl bridge and the pi-system of the azobenzene could be clearly assigned. This concept will be highly useful in designing more effective MOST systems in the future.
引用
收藏
页码:1145 / 1148
页数:4
相关论文
共 39 条
[11]   σ/σ- and π/π-Interactions Are Equally Important: Multilayered Graphanes [J].
Fokin, Andrey A. ;
Gerbig, Dennis ;
Schreiner, Peter R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) :20036-20039
[12]   Effect of the Damping Function in Dispersion Corrected Density Functional Theory [J].
Grimme, Stefan ;
Ehrlich, Stephan ;
Goerigk, Lars .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2011, 32 (07) :1456-1465
[13]   A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu [J].
Grimme, Stefan ;
Antony, Jens ;
Ehrlich, Stephan ;
Krieg, Helge .
JOURNAL OF CHEMICAL PHYSICS, 2010, 132 (15)
[14]   Photon energy storage materials with high energy densities based on diacetylene-azobenzene derivatives [J].
Han, Ggoch Ddeul ;
Park, Sarah S. ;
Liu, Yun ;
Zhitomirsky, David ;
Cho, Eugene ;
Dinca, Mircea ;
Grossman, Jeffrey C. .
JOURNAL OF MATERIALS CHEMISTRY A, 2016, 4 (41) :16157-16165
[15]   Selective switching of multiple azobenzenes [J].
Heindl, Andreas H. ;
Becker, Jonathan ;
Wegner, Hermann A. .
CHEMICAL SCIENCE, 2019, 10 (31) :7418-7425
[16]   ENERGY-STORAGE IN ORGANIC PHOTOISOMERS [J].
JONES, G ;
CHIANG, SH ;
XUAN, PT .
JOURNAL OF PHOTOCHEMISTRY, 1979, 10 (01) :1-18
[17]   AROMATIC AROMATIC INTERACTIONS - FREE-ENERGY PROFILES FOR THE BENZENE DIMER IN WATER, CHLOROFORM, AND LIQUID BENZENE [J].
JORGENSEN, WL ;
SEVERANCE, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4768-4774
[18]   Azobenzene-Functionalized Carbon Nanotubes As High-Energy Density Solar Thermal Fuels [J].
Kolpak, Alexie M. ;
Grossman, Jeffrey C. .
NANO LETTERS, 2011, 11 (08) :3156-3162
[19]  
Kucharski TJ, 2014, NAT CHEM, V6, P441, DOI [10.1038/nchem.1918, 10.1038/NCHEM.1918]
[20]  
Lennartson A, 2018, GREEN CHEM SUSTAIN T, P327, DOI 10.1007/978-981-10-5924-7_9