Orthogonal reactivity of thiols toward chlorovinylsilanes: selective thiol-ene chemistry

Jennings, Abby R.; Bassampour, Zahra S.; Patel, Anish G.; Son, David Y.

doi:10.1016/j.tetlet.2014.09.113

Cited by 5 publications

(4 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One class of gate dielectrics, inorganic oxide gate dielectrics, tends to exhibit a high dielectric constant ( k ) and strength with good chemical/thermal resistance. , However, a high temperature (>300 °C) and/or vacuum processes are generally needed to manufacture these types of materials. , In addition, these types of gate dielectrics contain polar moieties, which disturb the OSC to grow in highly stretched or long-range π-extended domains and adversely affect the OFET performance. , In particular, these polar moieties, such as hydroxyl groups, carboxyl groups, and acrylate groups, are activated as trapping sites, substantially degrading the electrical performance and stability of the OFETs, owing to decreased field-effect mobility (μ FET ), a shift in the threshold voltage ( V th ), and poor subthreshold swing (SS) and hysteresis behavior of the OFETs. , In addition, inorganic oxide materials are extremely vulnerable to mechanical bending stress , and to ambient air conditions that enable polar molecules (e.g., oxygen and water molecules) to easily permeate the OSC/dielectric interfaces, generating charge-trapping sites . For these reasons, polymeric gate dielectric materials are considered to be competitive alternatives for OFET-based devices.…”

Section: Introductionmentioning

confidence: 99%

“…14,15 In particular, these polar moieties, such as hydroxyl groups, carboxyl groups, and acrylate groups, are activated as trapping sites, substantially degrading the electrical performance and stability of the OFETs, owing to decreased field-effect mobility (μ FET ), a shift in the threshold voltage (V th ), and poor subthreshold swing (SS) and hysteresis behavior of the OFETs. 16,17 In addition, inorganic oxide materials are extremely vulnerable to mechanical bending stress 18,19 and to ambient air conditions that enable polar molecules (e.g., oxygen and water molecules) to easily permeate the OSC/dielectric interfaces, generating chargetrapping sites. 20 For these reasons, polymeric gate dielectric materials are considered to be competitive alternatives for OFET-based devices.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Facile Photo-cross-linking System for Polymeric Gate Dielectric Materials toward Solution-Processed Organic Field-Effect Transistors: Role of a Cross-linker in Various Polymer Types

Kwon

Tang

Shin

et al. 2020

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

Energy-efficient solution-processed organic field-effect transistors (OFETs) are highly sought after in the low-cost printing industry as well as for the manufacture of flexible and other next-generation devices. The fabrication of such electronic devices requires high-functioning insulating materials that are chemically and mechanically robust to avoid lowering insulating properties during the device fabrication process or utilization of devices. In this study, we report a facile, fluorinated, UV-assisted cross-linker series using a fluorophenyl azide (FPA), which reacts with the C–H groups of a conventional polymer. This demonstrates the application of the cross-linked films in OFET gate dielectrics. The effects of the cross-linkable chemical structure of the FPA series on the cross-linking chemistry, photopatternability, and dielectric properties of the resulting films are investigated for low/high-k or amorphous/crystalline polymeric gate dielectric materials. The characteristics of insulating layers and behavior of OFETs containing these cross-linked gate dielectrics (for example, leakage current density (J), hysteresis, and charge trap density) depend on the polymer type. Furthermore, an organic-based complementary inverter and various printable OFETs with excellent electrical characteristics are successfully fabricated. Thus, these reported cross-linkers that enable the solution process and patterning of well-developed conventional polymer dielectric materials are promising for the realization of a more sustainable next-generation industrial technology for flexible and printable devices.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Facile Photo-cross-linking System for Polymeric Gate Dielectric Materials toward Solution-Processed Organic Field-Effect Transistors: Role of a Cross-linker in Various Polymer Types

Kwon

Tang

Shin

et al. 2020

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

show abstract

“…Generally, end-functionalized polymers in dried films tend to be slowly grafted even at high temperatures because there is only one coupling site present on each polymeric molecule. In particular, ambient-air conditions, such as oxygen and humidity levels, should be carefully controlled to avoid the deactivation of limited coupling sites, particularly for air-sensitive chlorosilane-terminated polymers …”

Section: Introductionmentioning

confidence: 99%

“…In particular, ambient-air conditions, such as oxygen and humidity levels, should be carefully controlled to avoid the deactivation of limited coupling sites, particularly for air-sensitive chlorosilaneterminated polymers. 21 Unlike these one-point coupling polymers, binary vinyl copolymers containing multiple coupling sites can be quickly grafted to various oxide surfaces. 22−25 One of the most important coupling agents is 3-methacryloxypropyltrimethoxysilane (MPTS).…”

Section: Introductionmentioning

confidence: 99%

Air-Processable Silane-Coupled Polymers to Modify a Dielectric for Solution-Processed Organic Semiconductors

Jang

Jeon

et al. 2015

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

Poly(styrene-r-3-methacryloxypropyltrimethoxysilane) (PSMPTS) copolymers were synthesized by the free radical polymerization of styrene and 3-methacryloxypropyltrimethoxysilane (MPTS) for use as surface modifiers. PSMPTS copolymers were spun-cast onto a hydrophilic SiO2 layer and were then annealed at 150 °C in ambient air. The polystyrene (PS)-based copolymer, with a molecular weight of 32 700 g mol(-1) and approximately 30 MPTS coupling sites, was easily grafted onto the SiO2 surface after annealing periods longer than 1 min, yielding a physicochemically stable layer. On the untreated and polymer-treated dielectrics, spin-casting of an ultrasonicated poly(3-hexyl thiophene) (P3HT) solution yielded highly interconnected crystal nanofibrils of P3HT. The resulting organic field-effect transistors (OFETs) showed similar mobility values of 0.01-0.012 cm(2) V(-1) s(-1) for all surfaces. However, the threshold voltage (Vth) drastically decreased from +13 (for bare SiO2) to 0 V by grafting the PSMPTS copolymers to the SiO2 surface. In particular, the interfacial charge traps that affect Vth were minimized by grafting the 11 mol % MPTS-loaded copolymer to the polar dielectric surface. We believe that this ambient-air-processable silane-coupled copolymer can be used as a solution-based surface modifier for continuous, large-scale OFET fabrication.

show abstract

Controllable Superhydrophobic Coating on Cotton Fabric by UV Induced Thiol‐ene Reaction for Wettability Patterning and Device Metallization

Deng

Huang

Chen

et al. 2017

Adv Materials Inter

View full text Add to dashboard Cite

electrochemistry, chemical deposition, self-assemble, and so on. [5][6][7][8][9][10] A common strategy is to anchor low surface energy polymers on to the relatively high surface energy pristine fabrics. Previous research work has found that long-chain fluorochemicals are extremely effective in achieving superhydrophobic state, but there have been tighter regulations and cost concerns for the use of fluorochemicals. Therefore, there is an urgent demand for alternative nonfluorine-containing low surface energy materials in this regard. Moreover, superhydrophobic-superhydrophilic switching has attracted much attention for a series of potential applications. [11][12][13] The switching process can be triggered by light, heat, electric field, and so on. Among these, light stimulation has an advantage of ease of operation and high yield. As an example, UV-initiated click reaction possesses rapid reaction rates and are environmentally friendly. Different thiols with certain reac-

show abstract

Orthogonal reactivity of thiols toward chlorovinylsilanes: selective thiol-ene chemistry

Cited by 5 publications

References 22 publications

Facile Photo-cross-linking System for Polymeric Gate Dielectric Materials toward Solution-Processed Organic Field-Effect Transistors: Role of a Cross-linker in Various Polymer Types

Facile Photo-cross-linking System for Polymeric Gate Dielectric Materials toward Solution-Processed Organic Field-Effect Transistors: Role of a Cross-linker in Various Polymer Types

Air-Processable Silane-Coupled Polymers to Modify a Dielectric for Solution-Processed Organic Semiconductors

Controllable Superhydrophobic Coating on Cotton Fabric by UV Induced Thiol‐ene Reaction for Wettability Patterning and Device Metallization

Contact Info

Product

Resources

About