New tetrathiafulvalene fused-naphthalene diimides for solution-processible and air-stable p-type and ambipolar organic semiconductors

Tan, Luxi; Guo, Yunlong; Yang, Yang; Zhang, Guanxin; Zhang, Deqing; Yu, Gui; Xu, Wei; Liu, Yunqi

doi:10.1039/c2sc20303k

Cited by 70 publications

(54 citation statements)

References 87 publications

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“…[80] These important results for a new class of organic semiconductors resulted in much further work in the last few years, in which the synthesis of laterally extended NDI derivatives by substitution with dithioles or dithiolates was varied according to the same synthetic concept. Examples in this regard are the compound with peripheral cyanoacetate groups which is an analogue of 55, the derivative 57 that was obtained by six-membered-ring annulation with 1,4-dithiine-2,3-dicarbonitrile (Scheme 12), [79b] and Zhang developed sulfur-rich (for example 56 a, Scheme 11) [81] as well as laterally extended unsymmetric derivatives. [82] Depending on the position of their frontier molecular orbitals, these derivatives function as p-type, n-type, or ambipolar organic semiconductors.…”

Section: Lateral Ring Expansionmentioning

confidence: 99%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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Naphthalene diimides, which have for a long time been in the shadow of their higher homologues the perylene diimides, currently belong to the most investigated classes of organic compounds. This is primarily due to the initial synthetic studies on core functionalization that were carried out at the beginning of the last decade, which facilitated diverse structural modifications of the naphthalene scaffold. Compounds with greatly modified optical and electronic properties that can be easily and effectively modulated by appropriate functionalization were made accessible through relatively little synthetic effort. This resulted in diverse interesting applications. The electron-deficient character of these compounds makes them highly valuable, particularly in the field of organic electronics as air-stable n-type semiconductors, while absorption bands over the whole visible spectral range through the introduction of core substituents enabled interesting photosystems and photovoltaic applications. This Review provides an overview on different approaches towards core functionalization as well as on synthetic strategies for the core expansion of naphthalene diimides that have been developed mainly in the last five years.

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Section: Lateral Ring Expansionmentioning

confidence: 99%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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“…10,11,12 The contact between small 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 3 molecules in the solid state and degree of conjugation determined the charge-carrier mobility. 13,14 Among the several sets of conjugated materials, sulfur-based conjugated systems 15,16,17,18 are highly explored as p-type semiconducting materials. 19,20,21 Recently, selenium-based conjugated systems are being explored.…”

Section: Introductionmentioning

confidence: 99%

Selenium-Containing Fused Bicyclic Heterocycle Diselenolodiselenole: Field Effect Transistor Study and Structure–Property Relationship

Debnath

Chithiravel

Sharma

et al. 2016

ACS Appl. Mater. Interfaces

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The first application of the diselenolodiselenole (C4Se4) heterocycle as an active organic field effect transistor materials is demonstrated here. C4Se4 derivatives (2a-2d) were obtained by using a newly developed straightforward diselenocyclization protocol, which includes the reaction of diynes with selenium powder at elevated temperature. C4Se4 derivatives exhibit strong donor characteristics and planar structure (except 2d). The atomic force microscopic analysis and thin-film X-ray diffraction pattern of compounds 2a-2d indicated the formation of distinct crystalline films that contain large domains. A scanning electron microscopy study of compound 2b showed development of symmetrical grains with an average diameter of 150 nm. Interestingly, 2b exhibited superior hole mobility, approaching 0.027 cm(2) V(-1) s(-1) with a transconductance of 9.2 μS. This study correlate the effect of π-stacking, Se···Se intermolecular interaction, and planarity with the charge transport properties and performance in the field effect transistor devices. We have shown that the planarity in C4Se4 derivatives was achieved by varying the end groups attached to the C4Se4 core. In turn, optoelectronic properties can also be tuned for all these derivatives by end-group variation.

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“…Of these, the single crystal OFETs of 333 exhibited balanced hole and electron mobilities of higher than 0.1 cm 2 V −1 s −1 . Recently, a series of naphthalene-based semiconductors with ambipolar transport properties were developed by Zhang et al [311,407] [410]. Beside the suitable energy levels, semicrystallinity and highly ordered lamellar packing also favor the high and balanced ambipolar performance in 338-based OFETs.…”

Section: Selected Ambipolar Small-molecule Semiconductorsmentioning

confidence: 98%

Organic Semiconductors for Field-Effect Transistors

Zhang

2015

Lecture Notes in Chemistry

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An important application of organic semiconductors is to fabricate organic field-effect transistors (OFETs) which are essential building blocks for the next generation of organic circuits. In terms of molecular size or molecular weight, organic semiconductors can be divided into small-molecule and polymer semiconductors, and thus their corresponding OFETs can also be categorized into organic small molecule OFETs and polymer field-effect transistors (PFETs). On the basis of the main charge carriers transporting in OFET channels, organic semiconductors can be further divided into p-type, n-type, and ambipolar semiconducting materials. According to the characteristic of the organic semiconductors, the OFETs can be classified into two types: organic thin film transistors (OTFTs) and organic single crystal transistors. In any kind of OFET devices, organic semiconductor materials are the core; their properties determine the performance of the electronic devices. Therefore, the design and synthesis of high performance organic semiconductor materials are the basis and premise of the wide application of OFET devices. In the past few decades, great progress has been made in developing organic semiconductors. Besides organic semiconducting materials, there are many other factors influencing the performance of OFETs including device configuration, processing technique, and other devices physical factors, etc. In the following, a brief review of the development of p-type, n-type, ambipolar organic semiconductors and their field-effect properties is given. The history, mechanism, configuration, and fabrication methods of OFET devices and main performance influencing factors of OFETs are also introduced.

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New tetrathiafulvalene fused-naphthalene diimides for solution-processible and air-stable p-type and ambipolar organic semiconductors

Cited by 70 publications

References 87 publications

Strategies for the Synthesis of Functional Naphthalene Diimides

Strategies for the Synthesis of Functional Naphthalene Diimides

Selenium-Containing Fused Bicyclic Heterocycle Diselenolodiselenole: Field Effect Transistor Study and Structure–Property Relationship

Organic Semiconductors for Field-Effect Transistors

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