Liquid crystals from shape-persistent porphyrin stars with intrinsic free space

被引:16
作者
Ghosh, Tapas [1 ]
Gerbig, Lisa [1 ]
Lambov, Martin [1 ]
Dechant, Moritz [1 ]
Lehmann, Matthias [1 ,2 ]
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Wurzburg, Ctr Nanosyst Chem, D-97074 Wurzburg, Germany
关键词
SOLAR-CELLS; DERIVATIVES; COMPLEXES; BEHAVIOR; DIMER;
D O I
10.1039/c9tc07086a
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
A small library of shape-persistent, conjugated star-shaped liquid crystals (LCs) with a zinc porphyrin core was successfully synthesized. Different conjugated arms are attached in themeso-positions. The self-assembly is at the limit between liquid crystals and soft crystal phases owing to the space-filling requirement. A model indicates the formation of dimers in double helices. A remarkable mesogen with thiophene linked directly to the porphyrin core generates J-aggregates in solution, which persist in the solid state. In the liquid crystal the J-aggregates disappear but can be reversibly reobtained by solvent treatment.
引用
收藏
页码:5562 / 5571
页数:10
相关论文
共 53 条
[1]  
Cammidge A. N., 1998, HDB LIQUID CRYSTAL B, V2B
[2]  
Frisch M. J., 2016, GAUSSIAN16 REVISION
[3]   Columnar liquid-crystalline assemblies of X-shaped pyrene-oligothiophene conjugates: photoconductivities and mechanochromic functions [J].
Gan, Kian Ping ;
Yoshio, Masafumi ;
Kato, Takashi .
JOURNAL OF MATERIALS CHEMISTRY C, 2016, 4 (22) :5073-5080
[4]   An efficient one-flask synthesis of N-confused tetraphenylporphyrin [J].
Geier, GR ;
Haynes, DM ;
Lindsey, JS .
ORGANIC LETTERS, 1999, 1 (09) :1455-1458
[5]   High-Performance Near-Infrared Absorbing n-Type Porphyrin Acceptor for Organic Solar Cells [J].
Hadmojo, Wisnu Tantyo ;
Lee, Un-Hak ;
Yim, Dajeong ;
Kim, Hyun Woo ;
Jang, Woo-Dong ;
Yoon, Sung Cheol ;
Jung, In Hwan ;
Jang, Sung-Yeon .
ACS APPLIED MATERIALS & INTERFACES, 2018, 10 (48) :41344-41349
[6]   Artificial light-harvesting n-type porphyrin for panchromatic organic photovoltaic devices [J].
Hadmojo, Wisnu Tantyo ;
Yim, Dajeong ;
Aqoma, Havid ;
Ryu, Du Yeol ;
Shin, Tae Joo ;
Kim, Hyun Woo ;
Hwang, Eojin ;
Jang, Woo-Dong ;
Jung, In Hwan ;
Jang, Sung-Yeon .
CHEMICAL SCIENCE, 2017, 8 (07) :5095-5100
[7]   Avogadro: an advanced semantic chemical editor, visualization, and analysis platform [J].
Hanwell, Marcus D. ;
Curtis, Donald E. ;
Lonie, David C. ;
Vandermeersch, Tim ;
Zurek, Eva ;
Hutchison, Geoffrey R. .
JOURNAL OF CHEMINFORMATICS, 2012, 4
[8]   Liquid crystals for organic thin-film transistors [J].
Iino, Hiroaki ;
Usui, Takayuki ;
Hanna, Jun-ichi .
NATURE COMMUNICATIONS, 2015, 6
[9]   Characterization of porphyrin surface orientation in monolayers on au(111) and si(100) using spectroscopically labeled molecules [J].
Jiao, Jieying ;
Thamyongkit, Patchanita ;
Schmidt, Izabela ;
Lindsey, Jonathan S. ;
Bocian, David F. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2007, 111 (34) :12693-12704
[10]  
Kasha M., 1965, PURE APPL CHEM, V11, p371, DOI DOI 10.1351/PAC196511030371