Side chain structure affects the molecular packing and photovoltaic performance of oligothiophene-based solution-processable small molecules

RSC Advances ◽  
2015 ◽  
Vol 5 (83) ◽  
pp. 67718-67726 ◽  
Author(s):  
Shang-Che Lan ◽  
Chiao-Kai Chang ◽  
Yueh-Hsin Lu ◽  
Shu-Wei Lin ◽  
Alex K.-Y. Jen ◽  
...  
Keyword(s):  
Small Molecules ◽  
Intermolecular Interactions ◽  
Photovoltaic Performance ◽  
Thiobarbituric Acid ◽  
Chain Structure ◽  
Central Core ◽  
Side Chain ◽  
Side Chains ◽  
Alkyl Side Chains ◽  
Chain Lengths

Small molecules with alkyl side chains of different lengths were prepared with 2,2′-bithiophene, terthiophene and thiobarbituric acid as the central core, spacer and end-cap. Uniform, shorter chain lengths gave stronger intermolecular interactions, favoring crystallization.

n-Alkylresorcinol Occurrence in Mercurialis perennis L. (Euphorbiaceae)

2010 ◽  
Vol 65 (3-4) ◽  
pp. 174-179 ◽  
Author(s):  
Peter Lorenz ◽  
Matthias Knödler ◽  
Julia Bertrams ◽  
Melanie Berger ◽  
Ulrich Meyer ◽  
...  
Keyword(s):  
Side Chain ◽  
Side Chains ◽  
Alkyl Side Chain ◽  
Alkyl Side Chains ◽  
Chain Lengths ◽  
New View

Investigation of the dichloromethane extracts from herbal and root parts of Mercurialis perennis L. afforded a mixture of 11 homologous n-alkylresorcinols (ARs) with saturated odd-numbered alkyl side chains (C15:0-C27:0). In addition to three predominant ARs (C19:0, C21:0 and C23:0), a number of minor ARs were identified by use of LC-MS/MS and GC-MS techniques. Among the compounds detected, four uncommon ARs with evennumbered alkyl side chain lengths were also determined. The overall AR concentration in herbal parts was 7 to 9 times higher compared to that of the roots. The results presented may open a new view on the phytochemistry and pharmacognosy of M. perennis and other members of the Euphorbiaceae family.

scholarly journals The effect of branched versus linear alkyl side chains on the bulk heterojunction photovoltaic performance of small molecules containing both benzodithiophene and thienopyrroledione

2014 ◽  
Vol 16 (37) ◽  
pp. 19874-19883 ◽  
Author(s):  
Yu Jin Kim ◽  
Kwang Hun Park ◽  
Jong-jin Ha ◽  
Dae Sung Chung ◽  
Yun-Hi Kim ◽  
...  
Keyword(s):  
Small Molecules ◽  
Power Conversion Efficiency ◽  
Conversion Efficiency ◽  
Light Absorption ◽  
Bulk Heterojunction ◽  
Power Conversion ◽  
Photovoltaic Performance ◽  
Side Chains ◽  
Higher Power ◽  
Alkyl Side Chains

Compared toBDTO-TTPD,BDTEH-TTPDshowed stronger light absorption and longer-range ordering, which results in higher power conversion efficiency.

scholarly journals Synthesis of New Derivatives of BEDT-TTF: Installation of Alkyl, Ethynyl, and Metal-Binding Side Chains and Formation of Tris(BEDT-TTF) Systems

2021 ◽  
Vol 7 (8) ◽  
pp. 110
Author(s):  
Songjie Yang ◽  
Matteo Zecchini ◽  
Andrew Brooks ◽  
Sara Krivickas ◽  
Desiree Dalligos ◽  
...  
Keyword(s):  
Metal Binding ◽  
Tricarboxylic Acid ◽  
Metal Salts ◽  
Side Chain ◽  
Side Chains ◽  
Ethynyl Group ◽  
X Ray ◽  
Transition Metal Salts ◽  
Alkyl Side Chains ◽  
Derivatives Of

The syntheses of new BEDT-TTF derivatives are described. These comprise BEDT-TTF with one ethynyl group (HC≡C-), with two (n-heptyl) or four (n-butyl) alkyl side chains, with two trans acetal (-CH(OMe)2) groups, with two trans aminomethyl (-CH2NH2) groups, and with an iminodiacetate (-CH2N(CH2CO2−)2 side chain. Three transition metal salts have been prepared from the latter donor, and their magnetic properties are reported. Three tris-donor systems are reported bearing three BEDT-TTF derivatives with ester links to a core derived from benzene-1,3,5-tricarboxylic acid. The stereochemistry and molecular structure of the donors are discussed. X-ray crystal structures of two BEDT-TTF donors are reported: one with two CH(OMe)2 groups and with one a -CH2N(CH2CO2Me)2 side chain.

scholarly journals Controlled steric selectivity in molecular doping towards closest-packed supramolecular conductors

2020 ◽  
Vol 1 (1) ◽  
Author(s):  
Shinya Kohno ◽  
Yu Yamashita ◽  
Naotaka Kasuya ◽  
Tsubasa Mikie ◽  
Itaru Osaka ◽  
...  
Keyword(s):  
Conjugated Polymers ◽  
Steric Effects ◽  
Side Chain ◽  
Side Chains ◽  
Void Space ◽  
Alkyl Side Chains ◽  
Recent Developments ◽  
High Carrier ◽  
Molecular Doping ◽  
Steric Selectivity

Abstract Recent developments in molecular doping technologies allow extremely high carrier densities in polymeric semiconductors, exhibiting great diversity because of the unique size, conformation, and steric effect of molecular dopants. However, it is controversial how steric effects can limit the doping efficiency and to what extent dopants can be accommodated in polymers. Here, we employ two distinct conjugated polymers with different alkyl side-chain densities, where polymers are doped via anion-change, allowing greater variation in the incorporation of molecular dopants having different electrostatic potentials and shapes. We characterize the doping efficiency with regard to steric effects, considering the unique void space in the conjugated polymers. Our study reveals that doping efficiency of polymers with sparse alkyl side-chains is significantly greater than that with dense side-chains. A closest-packed supramolecule is realized with a particular combination of a sparse polymer and a large dopant, giving rise to high conductivity, air stability, and remarkably high work function. This work provides a critical insight into overcoming steric effects in molecular doping.

Bioengineering of emulsifier structure: emulsan analogs

1997 ◽  
Vol 43 (4) ◽  
pp. 384-390 ◽  
Author(s):  
Alexander Gorkovenko ◽  
Jinwen Zhang ◽  
Richard A. Gross ◽  
Alfred L. Allen ◽  
David L. Kaplan
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Carbon Source ◽  
Chain Length ◽  
Acinetobacter Calcoaceticus ◽  
Chain Structure ◽  
Fatty Acid Esters ◽  
Side Chain ◽  
Rag 1 ◽  
Chain Lengths

Strategies were investigated to modulate the side chain structure of emulsans formed by Acinetobacter calcoaceticus RAG-1. Analysis of emulsan fatty acid side chain groups by gas chromatography – mass spectrometry (GC–MS) revealed that by providing the exogenous n-alkanoic fatty acids 15:0, 16:0, and 17:0, emulsan analogs were formed with 53, 46, and 44 mol%, respectively, of fatty acid substituents with chain lengths equal to that of the carbon source. In contrast, the increase in emulsan fatty acids of chain lengths less than 15 or greater than 17 by providing corresponding shorter and longer chain length fatty acids as carbon sources was not substantial. When [1-13C]-labeled (99% enriched) palmitic acid was used as a carbon source along with acetate, analysis of m/z 75/14 and 87/88 isotopomer ratios by GC-MS indicated that 84 and 86% of the 16:0 and 16:1 (9-cis) side groups, respectively, were incorporated intact from the 16:0 carbon source. The percentage of 14-, 15-, 16-, 17-, and 18-carbon chain length fatty acid esters that were monounsaturated were 11, 26, 50, 70, and 85%, respectively. Based on the observed percentage of unsaturated chain length dependence and almost identical enrichment at C-1 of 16:0 and 16:1 (9-cis) side groups from [1-13C]-labeled experiments, it was concluded that desaturation of preformed n-alkanoic acids was the predominant mechanism of their formation. Further work established correlations between side chain structure and product emulsification specificity/activity, so that bioengineered emulsans with improved selectivity can now be formed.Key words: emulsan, Acinetobacter calcoaceticus RAG-1, fatty acids, direct incorporation, emulsification activity.

Low band gap conjugated polymers combining siloxane-terminated side chains and alkyl side chains: side-chain engineering achieving a large active layer processing window for PCE > 10% in polymer solar cells

2017 ◽  
Vol 5 (33) ◽  
pp. 17619-17631 ◽  
Author(s):  
Xuncheng Liu ◽  
Li Nian ◽  
Ke Gao ◽  
Lianjie Zhang ◽  
Lechi Qing ◽  
...  
Keyword(s):  
Conjugated Polymers ◽  
Active Layer ◽  
Polymer Solar Cells ◽  
Hole Transport ◽  
Random Copolymers ◽  
Side Chain ◽  
Active Layer Thickness ◽  
Side Chains ◽  
Alkyl Side Chains ◽  
Thickness Tolerance

Side-chain random copolymers show high 3-D hole transport and offer excellent active layer thickness tolerance.

Impact of the alkyl side chain position on the photovoltaic properties of solution-processable organic molecule donor materials

2016 ◽  
Vol 4 (30) ◽  
pp. 11747-11753 ◽  
Author(s):  
J. Zhang ◽  
X. W. Zhu ◽  
C. He ◽  
H. J. Bin ◽  
L. W. Xue ◽  
...  
Keyword(s):  
Organic Molecule ◽  
Side Chain ◽  
Side Chains ◽  
Alkyl Side Chain ◽  
Photovoltaic Properties ◽  
Alkyl Side Chains ◽  
Solution Processable ◽  
New Compounds

Two new compounds with alkyl side chains at different positions have a similar structure, but exhibit different photovoltaic properties.

scholarly journals Integrated multi-omics investigations reveal the key role of synergistic microbial networks in removing plasticizer di-(2-ethylhexyl) phthalate from estuarine sediments

2021 ◽  
Author(s):  
Sean Ting-Shyang Wei ◽  
Yi-Lung Chen ◽  
Yu-Wei Wu ◽  
Tien-Yu Wu ◽  
Yi-Li Lai ◽  
...  
Keyword(s):  
Phthalic Acid ◽  
Profile Analysis ◽  
Metabolite Profile ◽  
Degradation Pathway ◽  
Estuarine Sediments ◽  
Side Chain ◽  
Side Chains ◽  
Human Beings ◽  
Alkyl Side Chains ◽  
Ethylhexyl Phthalate

Di-(2-ethylhexyl) phthalate (DEHP) is the most widely used plasticizer worldwide with an annual global production of over eight million tons. Because of its improper disposal, endocrine-disrupting DEHP often accumulates in estuarine sediments in industrialized countries at sub-millimolar levels, resulting in adverse effects on both ecosystems and human beings. The microbial degraders and biodegradation pathways of DEHP in O2-limited estuarine sediments remain elusive. Here, we employed an integrated meta-omics approach to identify the DEHP degradation pathway and major degraders in this ecosystem. Estuarine sediments were treated with DEHP or its derived metabolites, o-phthalic acid and benzoic acid. The rate of DEHP degradation in denitrifying mesocosms was two times slower than that of o-phthalic acid, suggesting that side-chain hydrolysis of DEHP is the rate-limiting step of anaerobic DEHP degradation. On the basis of microbial community structures, functional gene expression, and metabolite profile analysis, we proposed that DEHP biodegradation in estuarine sediments is mainly achieved through synergistic networks between denitrifying proteobacteria. Acidovorax and Sedimenticola are the major degraders of DEHP side-chains; the resulting o-phthalic acid is mainly degraded by Aestuariibacter through the UbiD-dependent benzoyl-CoA pathway. We isolated and characterized Acidovorax sp. strain 210-6 and its extracellular hydrolase, which hydrolyzes both alkyl side-chains of DEHP. Interestingly, genes encoding DEHP/MEHP hydrolase and phthaloyl-CoA decarboxylase—key enzymes for side-chain hydrolysis and o-phthalic acid degradation, respectively—are flanked by transposases in these proteobacterial genomes, indicating that DEHP degradation capacity is likely transferred horizontally in microbial communities.

scholarly journals Unexpected Trends in the Hydrophobicity of Fluorinated Amino Acids Reflect Competing Changes in Polarity and Conformation

2018 ◽  
Author(s):  
João R. Robalo ◽  
Ana Vila Verde
Keyword(s):  
Amino Acids ◽  
Free Energy ◽  
Side Chain ◽  
Side Chains ◽  
Hydration Free Energy ◽  
Crossover Point ◽  
Fluorinated Amino Acids ◽  
Road Map ◽  
Alkyl Side Chains ◽  
The Impact

<div><div><div><p>Fluorination can dramatically improve the thermal and proteolytic stability of proteins and their enzymatic activity. Key to the impact of fluorination on protein properties is the hydrophobicity of fluorinated amino acids. We use molecular dynamics simulations, together with a new fixed-charge, atomistic force field, to quantify the changes in hydration free energy for amino acids with alkyl side chains and with 1 to 6 –CH to –CF side chain substitutions. Fluorination changes the hydration free energy by 1.5 to +2 kcal mol<sup>-</sup>1, but the number of fluorines is a poor predictor of hydrophobicity. Changes in hydration free energy reflect two main contributions: i) fluorination alters side chain-water interactions; we identify a crossover point from hydrophilic to hydrophobic fluoromethyl groups which may be used to estimate the hydrophobicity of fluorinated alkyl side-chains; ii) fluorination alters the number of backbone-water hydrogen bonds via changes in the relative side chain-backbone conformation. Our results offer a road map to mechanistically understand how fluorination alters hydrophobicity of (bio)polymers.</p></div></div></div>

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