Extensive intramolecular π-conjugation is considered to be requisite in the design of organic semiconductors. Here, two inkjet pigments, epindolidione and quinacridone, that break this design rule are explored. These molecules afford intermolecular π-stacking reinforced by hydrogen-bonding bridges. Air-stable organic field effect transistors are reported that support mobilities up to 1.5 cm(2)/Vs with T80 lifetimes comparable with the most stable reported organic semiconducting materials.
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http://dx.doi.org/10.1002/adma.201204039 | DOI Listing |
Sci Adv
October 2024
MOE Key Laboratory of Organic Integrated Circuits & Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, School of Sciences, Tianjin University, Tianjin 300072, China.
As a key component for wearable electronics, intrinsically stretchable and healable semiconducting polymers are scarce because carrier mobility is often reduced with increasing stretchability and self-healability. Here, we combine stepwise polymerization and thermal conversion to introduce in situ continuous hydrogen bonding sites in a polymer backbone without breaking the conjugation or introducing bulky softer side chains, benefiting the intrachain and interchain charge transport. We demonstrate that a regular sequence structure facilitated the formation of big nanofibers with a high degree of aggregation, providing the loose and porous thin film with simultaneously improved charge transport, stretchability, and self-healability.
View Article and Find Full Text PDFChem Sci
August 2024
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Integrated Research Consortium on Chemical Science (IRCCS), Nagoya University Furo-cho, Chikusa-ku Nagoya 464-8603 Japan
Significant effort has been devoted to the development of materials that combine high electrical conductivity and permanent porosity. This paper discloses a diazaporphyrin-based hydrogen-bonded organic framework (HOF) with porosity and n-type semiconductivity. A 5,15-diazaporphyrin Ni(ii) complex with carboxyphenyl groups at the positions afforded a HOF due to hydrogen-bonding interactions between the carboxy groups and -nitrogen atoms.
View Article and Find Full Text PDFACS Appl Mater Interfaces
April 2023
Department of Chemical Engineering, National Taiwan University, Taipei 10617, Taiwan.
J Am Chem Soc
May 2022
Instituto de Ciencia Molecular (ICMol), Universidad de Valencia, c/ Catedrático José Beltrán, 2, Paterna 46980, Spain.
Herein, we report on the use of tetrathiavulvalene-tetrabenzoic acid, HTTFTB, to engender semiconductivity in porous hydrogen-bonded organic frameworks (HOFs). By tuning the synthetic conditions, three different polymorphs have been obtained, denoted , , and , all of them presenting open structures (22, 15, and 27%, respectively) and suitable TTF stacking for efficient orbital overlap. Whereas collapses during the activation process, and offer high stability evacuation, with a CO sorption capacity of 1.
View Article and Find Full Text PDFChemistry
June 2022
Department of Chemistry & IRIS Adlershof, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 6, 12489, Berlin, Germany.
Semiconducting carbon nitride polymers are used in metal-free photocatalysts and in opto-electronic devices. Conventionally, they are obtained using thermal and ionothermal syntheses in inscrutable, closed systems and therefore, their condensation behavior is poorly understood. Here, the synthetic protocols and properties are compared for two types of carbon nitride materials - 2D layered poly(triazine imide) (PTI) and hydrogen-bonded melem hydrate - obtained from three low-melting salt eutectics taken from the systematic series of the alkali metal halides: LiCl/KCl, LiBr/KBr, and LiI/KI.
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