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

被引:47
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
来源
CHEMPLUSCHEM | 2019年 / 84卷 / 08期
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
[1]   Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].
Adamo, C ;
Barone, V .
JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (13) :6158-6170
[2]   Synthesis and Photochemical Properties of Oligo-ortho-azobenzenes [J].
Bellotto, Silvia ;
Reuter, Raphael ;
Heinis, Christian ;
Wegner, Hermann A. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) :9826-9834
[3]   o-Fluoroazobenzenes as Readily Synthesized Photoswitches Offering Nearly Quantitative Two-Way Isomerization with Visible Light [J].
Bleger, David ;
Schwarz, Jutta ;
Brouwer, Albert M. ;
Hecht, Stefan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (51) :20597-20600
[4]  
Chen CY, 2013, SCI REP-UK, V3, DOI [10.1038/srep02411, 10.1038/srep03260]
[5]   Molecularly Engineered Azobenzene Derivatives for High Energy Density Solid-State Solar Thermal Fuels [J].
Cho, Eugene N. ;
Zhitomirsky, David ;
Han, Grace G. D. ;
Liu, Yun ;
Grossman, Jeffrey C. .
ACS APPLIED MATERIALS & INTERFACES, 2017, 9 (10) :8679-8687
[6]  
Corruccini R.J., 1939, J. Am. Chem. Soc., V61, P2925
[7]   Azobenzene-based solar thermal fuels: design, properties, and applications [J].
Dong, Liqi ;
Feng, Yiyu ;
Wang, Ling ;
Feng, Wei .
CHEMICAL SOCIETY REVIEWS, 2018, 47 (19) :7339-7368
[8]   Photoswitchable Molecular Rings for Solar-Thermal Energy Storage [J].
Durgun, E. ;
Grossman, Jeffrey C. .
JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2013, 4 (06) :854-860
[9]   An energy-dense and thermal-stable bis-azobenzene/hybrid templated assembly for solar thermal fuel [J].
Feng, Wei ;
Li, Shipei ;
Li, Man ;
Qin, Chengqun ;
Feng, Yiyu .
JOURNAL OF MATERIALS CHEMISTRY A, 2016, 4 (21) :8020-8028
[10]   Photo-responsive carbon nanomaterials functionalized by azobenzene moieties: structures, properties and application [J].
Feng, Wei ;
Luo, Wen ;
Feng, Yiyu .
NANOSCALE, 2012, 4 (20) :6118-6134