Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights

2015 ◽  
Vol 3 (44) ◽  
pp. 11660-11674 ◽  
Author(s):  
Viktorija Mimaite ◽  
Juozas Vidas Grazulevicius ◽  
Rasa Laurinaviciute ◽  
Dmytro Volyniuk ◽  
Vygintas Jankauskas ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Organic Semiconductors ◽  
Hole Mobility ◽  
Methyl Groups

Methoxy and methyl groups are found to improve the hole mobility via hydrogen bonds. The corresponding mechanism is shown.

Efficient Electron Injection into Organic Semiconductors Induced by Hydrogen Bonds

2019 ◽  
pp. 840
Author(s):  
Hirohiko Fukagawa ◽  
Munehiro Hasegawa ◽  
Katsuyuki Morii ◽  
Kazuma Suzuki ◽  
Tsubasa Sasaki ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Organic Semiconductors ◽  
Electron Injection

scholarly journals 1-(5-Benzylsulfanyl-2,2-dimethyl-2,3-dihydro-1,3,4-thiadiazol-3-yl)-2,2-dimethylpropan-1-one

2012 ◽  
Vol 68 (4) ◽  
pp. o1228-o1228
Author(s):  
Mohd Sukeri Mohd Yusof ◽  
Fatimah Abdul Mutalib ◽  
Suhana Arshad ◽  
Ibrahim Abdul Razak
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Site Occupancy ◽  
Minor Component ◽  
Dihedral Angles ◽  
Methyl Groups ◽  
Compound C ◽  
Twist Conformation ◽  
Thiadiazole Ring ◽  
The Mean

In the title compound, C16H22N2OS2, the S atom of the thiadiazole ring and the attached methyl groups are disordered over two orientations with a refined site-occupancy ratio of 0.641 (11):0.359 (11). The thiadiazole ring is in a twist conformation in both disorder components. The mean plane through the thiadiazole ring makes dihedral angles of 77.39 (8) (major component) and 67.45 (11)° (minor component) with the benzene ring. Intramolecular C—H...N interactions generate twoS(6) ring motifs. In the crystal, molecules are linked by C—H...O hydrogen bonds into zigzag chains parallel to thebaxis.

Synthesis, crystal structure and molecular conformation of (±)-1-oxoferruginol and (±)-shonanol

2004 ◽  
Vol 219 (10) ◽  
Author(s):  
Swastik Mondal ◽  
Monika Mukherjee ◽  
Arnab Roy ◽  
Debabrata Mukherjee
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Diffraction Data ◽  
Molecular Conformation ◽  
Membered Ring ◽  
Methyl Groups ◽  
Single Bond ◽  
X Ray Diffraction ◽  
X Ray ◽  
Chemical Structures

Abstract(±)-1-oxoferruginol and (±)-shonanol, two potential intermediates in the synthesis of tricyclic diterpenoid ferruginol, have been prepared and crystal structures of the compounds have been investigated using single-crystal X-ray diffraction data. The methyl groups of the isopropyl moiety in (±)-shonanol are disordered over two positions with occupation factors 0.65(1) and 0.35(1), respectively. Although the chemical structures of two compounds are very similar, a C—C single bond in the terminal six-membered ring of (±)-1-oxoferruginol is replaced by a C=C bond in (±)-shonanol, the quantitative isostructurality index calculations indicate that the structures are not isostructural. Intermolecular O—H…O hydrogen bonds between pairs of molecules in the compounds related by center of inversion lead to characteristic dimers forming R

scholarly journals (E)-N-{3-[(m-Tolylimino)methyl]pyridin-2-yl}pivalamide

IUCrData ◽  
2017 ◽  
Vol 2 (11) ◽  
Author(s):  
Şehriman Atalay ◽  
Semra Gerçeker ◽  
Seher Meral
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Torsion Angle ◽  
Title Compound ◽  
Methyl Groups ◽  
Compound C ◽  
Benzene Rings

In the title compound, C18H21N3O, the dihedral angle between the pyridine and benzene rings is 30.53 (7)° and the C—C=N—C torsion angle is −170.6 (2)°. An intramolecular N—H...N hydrogen bond generates anS(6) ring. In the crystal, very weak C—H...O hydrogen bonds link the molecules intoC(8) [101] chains. Thetert-butyl methyl groups are disordered over two sets of sites in a 0.783 (4):0.217 (4) ratio.

scholarly journals (E)-3-Dimethylamino-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one

2012 ◽  
Vol 68 (6) ◽  
pp. o1712-o1713
Author(s):  
Mostafa M. Ghorab ◽  
Mansour S. Al-Said ◽  
Hazem A. Ghabbour ◽  
Tze Shyang Chia ◽  
Hoong-Kun Fun
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Thiophene Ring ◽  
Site Occupancy ◽  
Maximum Deviation ◽  
Methyl Groups ◽  
Π Interactions ◽  
Compound C

In the title compound, C11H15NOS, the 3-(dimethylamino)prop-2-en-1-one unit is approximately planar [maximum deviation = 0.0975 (14) Å] and its mean plane of seven non-H atoms makes a dihedral angle of 6.96 (10)° with the thiophene ring. In the crystal, molecules are linked by pairs of C—H...O hydrogen bonds into inversion dimers with R 2 2(14) ring motifs. The dimers are stacked along the c axis through C—H...π interactions. The two methyl groups, attached to the thiophene ring and the amino N atom, are each disordered over two orientations, with site-occupancy ratios of 0.59 (4):0.41 (4) and 0.74 (4):0.26 (4), respectively.

scholarly journals Organic Electronics: Universal Strategy for Efficient Electron Injection into Organic Semiconductors Utilizing Hydrogen Bonds (Adv. Mater. 43/2019)

2019 ◽  
Vol 31 (43) ◽  
pp. 1970308
Author(s):  
Hirohiko Fukagawa ◽  
Munehiro Hasegawa ◽  
Katsuyuki Morii ◽  
Kazuma Suzuki ◽  
Tsubasa Sasaki ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Organic Semiconductors ◽  
Organic Electronics ◽  
Electron Injection

scholarly journals Semiconducting polymer blends that exhibit stable charge transport at high temperatures

Science ◽  
2018 ◽  
Vol 362 (6419) ◽  
pp. 1131-1134 ◽  
Author(s):  
Aristide Gumyusenge ◽  
Dung T. Tran ◽  
Xuyi Luo ◽  
Gregory M. Pitch ◽  
Yan Zhao ◽  
...  
Keyword(s):  
High Temperature ◽  
Polymer Blends ◽  
Charge Transport ◽  
Organic Semiconductors ◽  
Room Temperature ◽  
Elevated Temperatures ◽  
Hole Mobility ◽  
General Strategy ◽  
Semiconducting Polymer ◽  
High Temperature Operation

Although high-temperature operation (i.e., beyond 150°C) is of great interest for many electronics applications, achieving stable carrier mobilities for organic semiconductors at elevated temperatures is fundamentally challenging. We report a general strategy to make thermally stable high-temperature semiconducting polymer blends, composed of interpenetrating semicrystalline conjugated polymers and high glass-transition temperature insulating matrices. When properly engineered, such polymer blends display a temperature-insensitive charge transport behavior with hole mobility exceeding 2.0 cm2/V·s across a wide temperature range from room temperature up to 220°C in thin-film transistors.

scholarly journals 3-Acetyl-1-(3-methylphenyl)thiourea

2012 ◽  
Vol 68 (8) ◽  
pp. o2574-o2574 ◽  
Author(s):  
B. Thimme Gowda ◽  
Sabine Foro ◽  
Sharatha Kumar
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Title Compound ◽  
Side Chain ◽  
Maximum Deviation ◽  
Methyl Groups ◽  
Compound C ◽  
Ring Motif

In the crystal structure of the title compound, C10H12N2OS, the conformation of the two N—H bonds areantito each other. The amide C=O and the C=S are are alsoantito each other. The N—H bond adjacent to the benzene ring issynto them-methyl groups. The dihedral angle between the benzene ring and the side chain [mean plane of atoms C—C(O)N—C—N; maximum deviation 0.029 (2) Å] is 14.30 (7)°. There is an intramolecular N—H...O hydrogen bond generating anS(6) ring motif. In the crystal, the molecules are linkedviaN—H...) hydrogen bonds, forming chains propagating along [001]. The S atom is disordered and was refined using a split model [occupancy ratio 0.56 (4):0.44 (4)].

scholarly journals Dynamic Infrared Electro-optic Response of Soluble Organic Semiconductors in Thin Film Transistors

2013 ◽  
Vol 1501 ◽  
Author(s):  
Emily G. Bittle ◽  
Joseph W. Brill ◽  
Joseph P. Straley
Keyword(s):  
Organic Semiconductors ◽  
Field Effect Transistors ◽  
Metal Layer ◽  
Hole Mobility ◽  
Atomic Layer ◽  
Semiconductor Films ◽  
Contact Impedance ◽  
Low Frequencies ◽  
Electro Optic ◽  
Linear Differential

ABSTRACTWe use a frequency-dependent electro-optic technique to measure the hole mobility in small molecule organic semiconductors, such as 6,13 bis(triisopropylsilylethynyl)-pentacene. Measurements are made on semiconductor films in bottom gate, bottom contact field-effect transistors (FETs.) Because of the buried metal layer effect the maximum response, due to absorption in the charge layer, will be for a dielectric film ∼ 1/4 of a wavelength (in the dielectric) (e.g. ∼ 1 micron thick in the infrared.) Results are presented for FETs prepared with both spin-cast polymer and alumina dielectrics prepared by atomic layer deposition. At low frequencies the results are fit to solutions to a non-linear differential equation describing the spatial dependence of flowing charge in the FET channel, which allows us to study multiple crystals forming across one set of drain-source contacts. FETs prepared on alumina dielectrics show interesting deviations from the model at high frequencies, possibly due to increased contact impedance.

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