scholarly journals Molecular Mimicry and Assemblies of Asymmetric Organic Semiconductors

Author(s):  
Craig Yu ◽  
Shohei Kumagai ◽  
Michitsuna Tsutsumi ◽  
Tadanori Kurosawa ◽  
Hiroyuki Ishii ◽  
...  

Abstract Molecular assembly is a crucial factor for charge transports in organic semiconductors (OSCs), and molecularly flexible alkyl chain substitution is a key design feature for achieving desired molecular assemblies. However, the high degree of freedom of alkyl chains leads to molecular fluctuations that are detrimental to OSC performances. Stabilization of alkyl chains via intermolecular interactions in packing structures exists in biological and materials systems, and such a strategy can be harnessed in OSCs to suppress molecular fluctuations. Here, we present a robust synthetic strategy for a series of asymmetric n-type benzo[de]isoquinolino[1,8-gh]quinolinetetracarboxylic diimide (BQQDI) OSCs with various alkyl chain lengths, and certain alkyl chains exhibit an unusual molecular mimicry with energetically favorable gauche conformer that shows isomorphic structures and small molecular fluctuations. Asymmetric n-type OSC with the optimum chain length exhibits satisfactory solubility, excellent electron mobility, and large-area single-crystalline thin films are fabricated for practical organic electronics.

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Sungjae Yoo ◽  
Jeongwon Kim ◽  
Sungwoo Choi ◽  
Doojae Park ◽  
Sungho Park

AbstractThe synthesis of highly complex two-dimensional (2D) metal nanoframes remains a great challenge. Synthetic strategies for preparing 2D metal nanoframes are few, and rational and systematic synthetic pathways to more complicated architectures have not yet been reported. Herein, we demonstrate a stepwise synthetic strategy for complex 2D metal nanoframes with a high degree of intricacy; the strategy leads to a variety of shapes, including rings, triangles, hexagons, and tripods with tailorable single or double frames in a single entity. These nanoframes of high homogeneity could be obtained through selective combination of four different chemical toolkits consisting of selective etching and deposition on certain facets, and concentric and/or eccentric regrowth by controlling the mismatches of lattice constants of metals. The resulting nanoframes were highly homogeneous in size and shape and had van der Waals interactions that maximized rim-to-rim contact, allowing them to uniquely self-assemble into large-area superstructures.


RSC Advances ◽  
2015 ◽  
Vol 5 (29) ◽  
pp. 22783-22791 ◽  
Author(s):  
Bo-Yu Chen ◽  
Yun-Chiao Huang ◽  
Jeng-Shiung Jan

Alkyl chain-grafted poly(l-lysine) vesicles with tunable molecular assembly were prepared by varying the polypeptide chain length and grafted alkyl chains.


2021 ◽  
Author(s):  
Shunsuke Ohtani ◽  
Natsumi Yamada ◽  
Masayuki Gon ◽  
Kazuo Tanaka ◽  
Yoshiki Chujo

We present systematic studies of the dependence of the red-to-near-infrared emission and stimuli-responsive properties of boron-fused azomethine conjugated copolymers on the lengths of the alkyl chains.


RSC Advances ◽  
2015 ◽  
Vol 5 (63) ◽  
pp. 50813-50820 ◽  
Author(s):  
Zhongquan Wan ◽  
Chunyang Jia ◽  
Yan Wang ◽  
Xiaojun Yao

Dithiafulvenyl–triphenylamine (DTF–TPA) based D-D-η-A organic dyes with different alkyl chains attached on the DTF unit were synthesized to investigate the effect of alkyl chain lengths on the photovoltaic performances of dye-sensitized solar cells.


Nanomaterials ◽  
2021 ◽  
Vol 11 (3) ◽  
pp. 593
Author(s):  
Oksana Petrichenko ◽  
Aiva Plotniece ◽  
Karlis Pajuste ◽  
Martins Rucins ◽  
Pavels Dimitrijevs ◽  
...  

This study was focused on the estimation of the targeted modification of 1,4-DHP core with (1) different alkyl chain lengths at 3,5-ester moieties of 1,4-DHP (C12, C14 and C16); (2) N-substituent at position 1 of 1,4-DHP (N-H or N-CH3); (3) substituents of pyridinium moieties at positions 2 and 6 of 1,4-DHP (H, 4-CN and 3-Ph); (4) substituent at position 4 of 1,4-DHP (phenyl and napthyl) on physicochemical properties of the entire molecules and on the characteristics of the obtained magnetoliposomes formed by them. It was shown that thermal behavior of the tested 1,4-DHP amphiphiles was related to the alkyl chains length, the elongation of which decreased their transition temperatures. The properties of 1,4-DHP amphiphile monolayers and their polar head areas were determined. The packing parameters of amphiphiles were in the 0.43–0.55 range. It was demonstrated that the structure of 1,4-DHPs affected the physicochemical properties of compounds. “Empty” liposomes and magnetoliposomes were prepared from selected 1,4-DHP amphiphiles. It was shown that the variation of alkyl chains length or the change of substituents at positions 4 of 1,4-DHP did not show a significant influence on properties of liposomes.


2012 ◽  
Vol 68 (4) ◽  
pp. o152-o155 ◽  
Author(s):  
Malcolm A. Kelland ◽  
Amber L. Thompson

Tetraisohexylammonium bromide [systematic name: tetrakis(4-methylpentyl)azanium bromide], C24H52N+·Br−, is a powerful structure II clathrate hydrate crystal-growth inhibitor. The crystal structure, in the space groupP3221, contains one ammonium cation and one bromide anion in the asymmetric unit, both on general positions. At 100 K, the ammonium cation exhibits one ordered isohexyl chain and three disordered isohexyl chains. At 250 K, all four isohexyl chains are disordered. In an effort to reduce the disorder in the alkyl chains, the crystal was thermally cycled, but the disorder remained, indicating that it is dynamic in nature.


RSC Advances ◽  
2021 ◽  
Vol 11 (21) ◽  
pp. 12641-12648
Author(s):  
Renyuan Chen ◽  
Caidie Xu ◽  
Yihao Lei ◽  
Hongxin Liu ◽  
Yabin Zhu ◽  
...  

A family of low molecular weight gelators with different alkyl chain lengths was constructed, having excellent gelation ability and antibiotic loading capacity. A low molecular weight hydrogelator was obtained by adjusting the length of alkyl chain.


2011 ◽  
Vol 474-476 ◽  
pp. 537-542
Author(s):  
Ti Feng Jiao ◽  
Xu Hui Li ◽  
Jing Xin Zhou ◽  
Yuan Yuan Xing ◽  
Jing Ren

Two functional azobenzene derivatives with alkyl chains and different substituted groups have been synthesized and their photoisomerization have also been investigated. It has been found that depending on the alkyl chain and different substituted groups, the formed azobenzene derivatives showed different properties, indicating distinct regulation of molecular skeletons. UV and IR data confirmed commonly the characteristic absorption of alkyl chain and aromatic segments in molecular structures. Thermal analysis demonstrated that the structural influence of both compounds in different temperature ranges. The difference of thermal stability is mainly attributed to the formation of Schiff base group and different substituent groups in molecular structure. The photoisomerization of these compounds both in solution and in cast film can undergo trans-to-cis isomerization by UV light irradiation, depending on different substituted groups. The present results have demonstrated that the special properties of azobenzene derivatives can be effectively turned by modifying molecular structures of objective compounds with proper substituted groups, which show potential application in functional material field.


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