The effect of hexyl side chains on molecular conformations, crystal packing, and charge transport of oligothiophenes

2017 ◽  
Vol 5 (3) ◽  
pp. 582-588 ◽  
Author(s):  
Benjamin P. Cherniawski ◽  
Steven A. Lopez ◽  
Edmund K. Burnett ◽  
Ilhan Yavuz ◽  
Lei Zhang ◽  
...  
Keyword(s):  
Charge Transport ◽  
Crystal Packing ◽  
Substituent Effects ◽  
Side Chains ◽  
Molecular Conformations ◽  
Conformational Preferences

We report substituent effects on conformational preferences and hole mobilities of 2,5-bis-(thiophen-2-yl) thieno[3,2-b]thiophenes (BTTT) monomer and dimer, and hexyl derivatives.

Impact of morphology, side-chains, and crystallinity on charge-transport properties of π-extended double helicenes

2019 ◽  
Vol 21 (2) ◽  
pp. 901-914 ◽  
Author(s):  
Ilhan Yavuz ◽  
Janice B. Lin ◽  
K. N. Houk
Keyword(s):  
Charge Transport ◽  
Transport Properties ◽  
Crystal Packing ◽  
Computational Study ◽  
Side Chain ◽  
Side Chains

We report a computational study on the effect of side-chain substitution, heteroaromatic substitution and unique crystal packing on the charge transport and mobility of three double helicene molecules.

Theoretical study of charge-transport and optical properties of indeno[1,2-b]fluorene-6,12-dione-based semiconducting materials

2018 ◽  
Vol 74 (6) ◽  
pp. 705-711 ◽  
Author(s):  
Jin-Dou Huang ◽  
Jinfeng Zhao ◽  
Kun Yu ◽  
Xiaohua Huang ◽  
Shi-Bo Cheng ◽  
...  
Keyword(s):  
Optical Properties ◽  
Charge Transport ◽  
Near Infrared ◽  
Reorganization Energy ◽  
Hole Mobility ◽  
Side Chains ◽  
Semiconducting Materials ◽  
Π Stacking ◽  
Electron Transfer Theory ◽  
Reorganization Energies

The conducting and optical properties of a series of indeno[1,2-b]fluorene-6,12-dione (IFD)-based molecules have been systematically studied and the influences of butyl, butylthio and dibutylamino substituents on the reorganization energies, intermolecular electronic couplings and charge-injection barriers of IFD have been discussed. The quantum-chemical calculations combined with electron-transfer theory reveal that the incorporation of sulfur-linked side chains decreases reorganization energy associated with hole transfer and optimizes intermolecular π–π stacking, which results in excellent ambipolar charge-transport properties (μh = 1.15 cm2 V−1 s−1 and μe = 0.08 cm2 V−1 s−1); in comparison, addition of dibutylamino side chains increases intermolecular steric interactions and hinders perfect intermolecular π–π stacking, which results in the weak electronic couplings and finally causes the low intrinsic hole mobility (μh = 0.01 cm2 V−1 s−1). Furthermore, electronic spectra of butyl-IFD, butylthio-IFD and dibutylamino-IFD were simulated and compared with the reported experimental data. Calculations demonstrate that IFD-based molecules possess potential for developing novel infrared and near-infrared probe materials via suitable chemical modifications.

High-performance near-infrared organic phototransistors based on diketopyrrolopyrrole conjugated polymers with partial removal of long branched alkyl side chains

2020 ◽  
Vol 8 (47) ◽  
pp. 16915-16922
Author(s):  
Yu Tang ◽  
Weijie Ge ◽  
Ping Deng ◽  
Qiaoming Zhang ◽  
Yingjie Liao ◽  
...  
Keyword(s):  
Conjugated Polymers ◽  
Charge Transport ◽  
High Performance ◽  
Near Infrared ◽  
Side Chains ◽  
Partial Removal ◽  
Nir Absorption ◽  
Alkyl Side Chains

Near-infrared (NIR) phototransistors based on diketopyrrolopyrrole polymers with partial removal of side chains are reported with improved NIR photoresponses, which take advantage of both strengthened NIR absorption and improved charge transport.

scholarly journals Molecular tectonics: homochiral 1D and 2D cadmium based coordination networks

CrystEngComm ◽  
2019 ◽  
Vol 21 (15) ◽  
pp. 2534-2540
Author(s):  
Patrick Larpent ◽  
Abdelaziz Jouaiti ◽  
Nathalie Kyritsakas ◽  
Mir Wais Hosseini
Keyword(s):  
Crystal Packing ◽  
Side Chains ◽  
Coordination Networks ◽  
Enantiomerically Pure ◽  
Molecular Tectonics

By combining enantiomerically pure tectons with Cd(NO3)2, a series of six new homochiral luminescent coordination networks are formed. The dimensionality and crystal packing of the latter are modulated by both the nature of the chiral side chains and the crystallization solvents.

Fine-Tuning of Crystal Packing and Charge Transport Properties of BDOPV Derivatives through Fluorine Substitution

2015 ◽  
Vol 137 (50) ◽  
pp. 15947-15956 ◽  
Author(s):  
Jin-Hu Dou ◽  
Yu-Qing Zheng ◽  
Ze-Fan Yao ◽  
Zhi-Ao Yu ◽  
Ting Lei ◽  
...  
Keyword(s):  
Charge Transport ◽  
Transport Properties ◽  
Crystal Packing ◽  
Fine Tuning ◽  
Fluorine Substitution

scholarly journals Symmetry Breaking in Side Chains Leading to Mixed Orientations and Improved Charge Transport in Isoindigo-alt-Bithiophene Based Polymer Thin Films

2017 ◽  
Vol 9 (30) ◽  
pp. 25426-25433 ◽  
Author(s):  
Guobiao Xue ◽  
Xikang Zhao ◽  
Ge Qu ◽  
Tianbai Xu ◽  
Aristide Gumyusenge ◽  
...  
Keyword(s):  
Thin Films ◽  
Symmetry Breaking ◽  
Charge Transport ◽  
Polymer Thin Films ◽  
Side Chains

Electroluminescence from New Polynorbornenes That Contain Blue-Light-Emitting and Charge-Transport Side Chains

1997 ◽  
Vol 30 (12) ◽  
pp. 3553-3559 ◽  
Author(s):  
Thomas J. Boyd ◽  
Yves Geerts ◽  
Jin-Kyu Lee ◽  
Deryn E. Fogg ◽  
Gino G. Lavoie ◽  
...  
Keyword(s):  
Charge Transport ◽  
Blue Light ◽  
Side Chains ◽  
Light Emitting

scholarly journals Substrate Induced Polymorphism in Organic Thin Films

2014 ◽  
Vol 70 (a1) ◽  
pp. C728-C728
Author(s):  
Basab Chattopadhyay ◽  
Yves Geerts
Keyword(s):  
Thin Film ◽  
Thin Films ◽  
Liquid Crystal ◽  
Charge Transport ◽  
Field Effect Transistors ◽  
Crystal Packing ◽  
Morphological Changes ◽  
Solid Substrate ◽  
Experimental Proof ◽  
Discotic Liquid Crystal

The presence of substrate induced polymorphic phases in thin films is an intriguing phenomenon with the physical and chemical factors responsible for its formation are not yet clearly understood. In particular, this is really crucial in the field of organic electronics, where the charge-transport properties are highly dependent on crystal packing, especially for organic field-effect transistors where charge transport occurs at the interface between the organic semiconductor and the dielectric. In pharmaceutical sector, thin film drug delivery is the new emerging alternative to traditional tablets and oral suspensions. The need to identify and control polymorphism induced by the substrate is thus very crucial. In this presentation, we report the structure and morphological changes associated with a substrate induced polymorphic phases in a discotic liquid crystal and a rod shaped DPP-thiophene-based molecule [1, 2]. The bulk compound and the thin films are characterized by a combination of various X-ray diffraction methods to investigate the structural properties. Atomic force microscopy and polarized optical microscopy are used to determine the thin film morphologies. This is the first experimental proof of presence of a substrate induced phase in discotic liquid crystal showcasing an unique example where the 2-D liquid crystalline phase converts to a 3-D crystal plastic phase due to nucleation caused by the solid substrate over a time scale of a month or longer. The presentation also highlights the importance of polymorphism in DPP-thiophene-based material and the specific organization that could arise from the interaction with the substrate depending on the growing conditions. Here the exact structural and the spectroscopic signatures of different polymorphic forms in bulk and in thin films could be identified. These are clearly factors to consider to induce the formation of a particular polymorph and to help to design deposition methodologies.

Conformation and tautomerism of methoxy-substituted 4-phenyl-4-thiazoline-2-thiones: a combined crystallographic andab initioinvestigation

2016 ◽  
Vol 72 (5) ◽  
pp. 421-425 ◽  
Author(s):  
Monaem Balti ◽  
Bernadette Norberg ◽  
Mohamed Lotfi Efrit ◽  
Steve Lanners ◽  
Johan Wouters
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Solid State ◽  
Ab Initio ◽  
Gas Phase ◽  
Medicinal Chemistry ◽  
Crystal Packing ◽  
Lead Compound ◽  
Molecular Conformations ◽  
Pharmaceutical Compound

4-Phenyl-4-thiazoline-2-thiol is an active pharmaceutical compound, one of whose activities is as a human indolenamine dioxygenase inhibitor. It has been shown recently that in both the solid state and the gas phase, the thiazolinethione tautomer should be preferred. As part of both research on this lead compound and a medicinal chemistry program, a series of substituted arylthiazolinethiones have been synthesized. The molecular conformations and tautomerism of 4-(2-methoxyphenyl)-4-thiazoline-2-thione and 4-(4-methoxyphenyl)-4-thiazoline-2-thione, both C10H9NOS2, are reported and compared with the geometry deduced fromab initiocalculations [PBE/6-311G(d,p)]. Both the crystal structure analyses and the calculations establish the thione tautomer for the two substituted arylthiazolinethiones. In the crystal structure of the 2-methoxyphenyl regioisomer, the thiazolinethione unit was disordered over two conformations. Both isomers exhibit similar hydrogen-bond patterns [R22(8) motif] and form dimers. The crystal packing is further reinforced by short S...S interactions in the 2-methoxyphenyl isomer. The conformations of the two regioisomers correspond to stable geometries calculated from anab initioenergy-relaxed scan.

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