scholarly journals Layered‐Herringbone Polymorphs and Alkyl‐Chain Ordering in Molecular Bilayer Organic Semiconductors

2019 ◽  
Vol 30 (4) ◽  
pp. 1906406 ◽  
Author(s):  
Shunto Arai ◽  
Kaede Morita ◽  
Jun'ya Tsutsumi ◽  
Satoru Inoue ◽  
Mutsuo Tanaka ◽  
...  
Keyword(s):  
Organic Semiconductors ◽  
Alkyl Chain ◽  
Chain Ordering

scholarly journals Molecular Mimicry and Assemblies of Asymmetric Organic Semiconductors

2021 ◽  
Author(s):  
Craig Yu ◽  
Shohei Kumagai ◽  
Michitsuna Tsutsumi ◽  
Tadanori Kurosawa ◽  
Hiroyuki Ishii ◽  
...  
Keyword(s):  
Organic Semiconductors ◽  
Alkyl Chain ◽  
Molecular Mimicry ◽  
Design Feature ◽  
Molecular Assembly ◽  
Large Area ◽  
Alkyl Chains ◽  
Synthetic Strategy ◽  
Chain Lengths ◽  
High Degree

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.

scholarly journals A new family of liquid and solid guanidine-based n-type dopants for solution-processed perovskite solar cells

2020 ◽  
Vol 4 (12) ◽  
pp. 3616-3622
Author(s):  
Hidenori Nakayama ◽  
Julia A. Schneider ◽  
Mina Faust ◽  
Hengbin Wang ◽  
Javier Read de Alaniz ◽  
...  
Keyword(s):  
Thermal Stability ◽  
Solar Cells ◽  
Physical Properties ◽  
Organic Semiconductors ◽  
Alkyl Chain ◽  
Perovskite Solar Cells ◽  
Solution Processed ◽  
New Family

A new family of n-type dopants for organic semiconductors is reported. Changing the alkyl chain of these triazabicyclodecene (TBD) dopants alters their physical properties, including thermal stability, and influences their doping efficiency.

Enhanced Layered-Herringbone Packing due to Long Alkyl Chain Substitution in Solution-Processable Organic Semiconductors

2017 ◽  
Vol 29 (3) ◽  
pp. 1245-1254 ◽  
Author(s):  
Hiromi Minemawari ◽  
Mutsuo Tanaka ◽  
Seiji Tsuzuki ◽  
Satoru Inoue ◽  
Toshikazu Yamada ◽  
...  
Keyword(s):  
Organic Semiconductors ◽  
Alkyl Chain ◽  
Solution Processable ◽  
Long Alkyl Chain

Molecular Requirements for Printable Organic Semiconductors in 7-Alkyl-2-phenyl[1]benzothieno[3,2-b][1]benzothiophenes (Ph-BTBT-Cn’s)

MRS Advances ◽  
2016 ◽  
Vol 1 (38) ◽  
pp. 2653-2658
Author(s):  
S. Inoue ◽  
H. Minemawari ◽  
J. Tsutsumi ◽  
T. Hamai ◽  
S. Arai ◽  
...  
Keyword(s):  
Chain Length ◽  
Organic Semiconductors ◽  
Field Effect ◽  
High Performance ◽  
Carrier Transport ◽  
Alkyl Chain ◽  
Field Effect Transistors ◽  
Systematic Investigation ◽  
Alkyl Chain Length

ABSTRACTHere we discuss requirements for high performance and solution processable organic semiconductors, by presenting a systematic investigation of 7-alkyl-2-phenyl[1]benzothieno[3,2-b][1]benzothiophenes (Ph-BTBT-Cn’s). We found that the solubility and thermal properties of Ph-BTBT-Cn’s depend systematically on the substituted alkyl-chain length n. The observed features are well understood in terms of the change of molecular packing motif with n: The compounds with n ≤ 4 do not form independent alkyl chain layers, whereas those with n ≥ 5 form isolated alkyl chain layers. The latter compounds afford a series of isomorphous bilayer-type crystal structures that form two-dimensional carrier transport layers within the crystals. We also show that the Ph-BTBT-C10 afford high performance single-crystalline field-effect transistors the mobility of which reaches as high as 15.9 cm2/Vs. These results demonstrate a crucial role of the substituted alkyl chain length for obtaining high performance organic semiconductors and field-effect transistors.

scholarly journals Naphthalimide end capped anthraquinone based solution-processable n-channel organic semiconductors: effect of alkyl chain engineering on charge transport

2018 ◽  
Vol 6 (14) ◽  
pp. 3774-3786 ◽  
Author(s):  
Thu-Trang Do ◽  
Yasunori Takeda ◽  
Sergei Manzhos ◽  
John Bell ◽  
Shizuo Tokito ◽  
...  
Keyword(s):  
Thin Film ◽  
Charge Transport ◽  
Small Molecules ◽  
Chain Length ◽  
Organic Semiconductors ◽  
Alkyl Chain ◽  
Thin Film Transistor ◽  
Alkyl Chain Length ◽  
Organic Thin Film ◽  
Organic Thin Film Transistor

A series of electron deficient small molecules using fused anthraquinone and naphthalimide conjugated backbone with different alkyl chain length with lower LUMO for n-channel organic thin film transistor.

scholarly journals Effects of Cholesterol on Water Permittivity of Biomimetic Ion Pair Amphiphile Bilayers: Interplay between Membrane Bending and Molecular Packing

2019 ◽  
Vol 20 (13) ◽  
pp. 3252
Author(s):  
Wu-jhao Tien ◽  
Kun-you Chen ◽  
Fong-yin Huang ◽  
Chi-cheng Chiu
Keyword(s):  
Alkyl Chain ◽  
Synergistic Effects ◽  
Deformation Energy ◽  
Ion Pair ◽  
Molecular Packing ◽  
Energy Penalty ◽  
Membrane Bending ◽  
Dynamics Simulations ◽  
Chain Ordering ◽  
Ion Pair Amphiphile

Ion pair amphiphile (IPA), a molecular complex composed of a pair of cationic and anionic amphiphiles, is an inexpensive phospholipid substitute to fabricate vesicles with various pharmaceutical applications. Modulating the physicochemical and permeation properties of IPA vesicles are important for carrier designs. Here, we applied molecular dynamics simulations to examine the cholesterol effects on the structures, mechanics, and water permittivity of hexadecyltrimethylammonium-dodecylsulfate (HTMA-DS) and dodecyltrimethylammonium- hexadecylsulfate (DTMA-HS) IPA bilayers. Structural and mechanical analyses indicate that both IPA systems are in gel phase at 298 K. Adding cholesterol induces alkyl chain ordering around the rigid sterol ring and increases the cavity density within the hydrophilic region of both IPA bilayers. Furthermore, the enhanced alkyl chain ordering and the membrane deformation energy induced by cholesterol increase the permeation free energy penalty. In contrast, cholesterol has minor effects on the water local diffusivities within IPA membranes. Overall, the cholesterol reduces the water permittivity of rigid IPA membranes due to the synergistic effects of increased alkyl chain ordering and enhanced membrane mechanical modulus. The results provide molecular insights into the effects of molecular packing and mechanical deformations on the water permittivity of biomimetic IPA membranes, which is critical for designing IPA vesicular carriers.

Directing Alkyl Chain Ordering of Functional Phosphorus Coupling Agents on ZrO2

Langmuir ◽  
2011 ◽  
Vol 27 (7) ◽  
pp. 3534-3540 ◽  
Author(s):  
Christoph J. Lomoschitz ◽  
Bernhard Feichtenschlager ◽  
Norbert Moszner ◽  
Michael Puchberger ◽  
Klaus Müller ◽  
...  
Keyword(s):  
Alkyl Chain ◽  
Coupling Agents ◽  
Chain Ordering

Spectroscopic Metrics for Alkyl Chain Ordering in Lying-Down Noncovalent Monolayers of Diynoic Acids on Graphene

2018 ◽  
Vol 30 (8) ◽  
pp. 2506-2514 ◽  
Author(s):  
Shane R. Russell ◽  
Tyson C. Davis ◽  
Jae Jin Bang ◽  
Shelley A. Claridge
Keyword(s):  
Alkyl Chain ◽  
Chain Ordering ◽  
Lying Down
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