Alternating Copolymers Incorporating Dithienogemolodithiophene for Field-Effect Transistor Applications

Shaw, Jessica; Zhong, Hongliang; Yau, Chin Pang; Casey, Abby; Buchaca‐Domingo, Ester; Stingelin, Natalie; Sparrowe, David; Mitchell, William J.; Heeney, Martin

doi:10.1021/ma5021038

Cited by 23 publications

(21 citation statements)

References 54 publications

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“…63,69,[85][86][87][88][89][90] The previously mentioned polymer 21 originally synthesized by Heeney and coworkers was also examined as a component of TFTs with a promising mobility of 0.11 cm 2 V -1 s -1 noted. 87 Similarly, the previously described dithienogermole and germafluorene copolymers 54-60 ( Fig.…”

Section: Transistors and Semi-conducting Materialsmentioning

confidence: 99%

“…105 Compound 87 was also incorporated into an OLED device with an overall device efficiency for blue electroluminescence of 3.4 %. In addition to several germanium-substituted dithienogermoles (88)(89)(90)(91), a number of oxo-bridged dithienogermole tetramers were also synthesized by the Ohshita group (92-94, Fig. 7) and a photoluminescent quantum yield of 80 % (λ em = 482 nm) was noted in one analogue (94).…”

Section: Light Emitting Materialsmentioning

confidence: 99%

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Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications

2016

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This review article summarizes recent progress in the synthesis and optoelectronic properties of conjugated materials containing heavy main group elements from Group 13-16 as integral components. As will be discussed, the introduction of these elements can promote novel phosphorescent behavior and support desirable molecular and polymeric properties such as low optical band gaps and high charge mobilities for photovoltaic and thin film transistor applications.

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Section: Transistors and Semi-conducting Materialsmentioning

confidence: 99%

Section: Light Emitting Materialsmentioning

confidence: 99%

Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications

2016

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“…followed by preparative GPC with toluene as the eluent to give DTG3T in26 %y ield (317 mg, 0.340 mmol) as ay ellow solid. HNMR (in CDCl 3 ,4 00 MHz): d = 7.30 (2 H, d, terthienyl, J = 3.6 Hz), 7.28 (2 H, s, DTG), 7.24 (2 H, d, terthienyl, J = 3.6 Hz), 7.07 (2 H, d, terthienyl, J = 3.8 Hz), 7.01-6.96 (4 H, m, terthienyl), 6.71-6.69 (2 H, m, terthienyl), 2.83 (4 H, q, C-CH 2 , J = 7.5 Hz), 1.32 (6 H, t, C-CH 3 , J = 7.5 Hz), 0.34 ppm (18 H, s, Si-CH 3 ).…”

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confidence: 99%

Intramolecular Energy Transfer in Dithienogermole Derivatives

Adachi

Nomura

Ohshita

2019

Chemistry A European J

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Dithienogermole (DTG) has been applied asa useful building unit of optical/semiconducting materials for organic optoelectronic devicesb ecause of its extended conjugation, high chemical stability,a nd good emissive properties. Although DTG has two substituents on the Ge atom, the substituents have been limitedt os imple alkyl and aryl groups in previousw ork. In this work, to further uncover the new functionalities of this useful building unit, various pconjugated groups were introduced on Ge of DTG.Itwas expected that the introduction of p-conjugated groups would give rise to efficient energy transfer between the substituents andt he DTG core, which are in proximity and linked by aG ea tom. The thus-prepared DTG compounds with fluo-rene, terthiophene, and pyrene units on Ge possessed wellseparatedf rontier orbitals on the substituents and the DTG core, as provedb yt he absorption spectra and DFT calculations. The substituted DTG derivativess howedc leare mission only from the energya cceptor even though the energy donor was photoexcited. This indicated theh ighly efficient energy transfer in these compounds. We also prepared more p-extended compound DTGFl2-Ph with phenyl groups on the DTG thiophener ings. DTGFl2-Ph showeds trong emission in the visible region with efficient energy transfer properties. These resultsc learly indicate the potential application of the present DTG system as optical functionalmaterials.[a] Dr.Y .A dachi, T.Scheme1.Synthetic route to DTG structure.Scheme2.Structuralmoleculardesign of prior work and the present study.

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“…[9] This is one of the reasonsw hy thienoacenes, especially those with thieno[3,2-b]thiophene units, have become popular in recent years. [10][11][12][13][14][15] In particular,an ew planar heteroacene building block, dithieno[2,3-d;2',3'd']benzo-[1,2-b;3,4-b']dithiophene (DTmBDT) [16] was designed to address solubility issues by introducing alkyl chains at the bay positions and to enhancet he possibilities for chemical functionalization at the terminal positions (without disturbing the planarity of the core) for various applications in organic electronics. [17][18][19] Therefore, it is intriguing to prepares pin-bearing DTmBDT molecules and to study their structures and inherent properties.…”

Section: Introductionmentioning

confidence: 99%

The Design of Radical Stacks: Nitronyl‐Nitroxide‐Substituted Heteropentacenes

et al. 2017

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The first alkyl chain‐anchored heteropentacene, dithieno[2,3‐d;2′,3′‐d′]benzo‐[1,2‐b;3,4‐b′]dithiophene (DTmBDT), mono‐ or disubstituted with a nitronyl nitroxide group has been prepared through a cross‐coupling synthetic procedure of the corresponding dibromo‐derivative (Br2‐DTmBDT) with a nitronyl nitroxide‐2‐ide gold(I) complex. The synthesized nitroxides possess high kinetic stability, which allowed us to investigate their structure and thermal, optical, electrochemical, and magnetic properties. Single‐crystal X‐ray diffraction of both mono‐ and diradicals revealed that the nitronyl nitroxide group lies almost in the same plane as the nearest side thiophene ring. Such arrangement favors formation of edge‐to‐edge dimers, which then form close π‐stacks surrounded by interdigitating alkyl chains. Before melting, these nitronyl nitroxide radical substituted molecules undergo at least two different phase transitions (PTs): for the monoradical, PTs are reversible, accompanied by hysteresis, and occur near 13 and 83 °C; the diradical upon heating shows a reversible PT with hysteresis in the temperature range 2–11 °C and an irreversible PT near 135 °C. PTs of this type are absent in Br2‐DTmBDT. Therefore, the step‐by‐step substitution of bromine atoms by nitronyl nitroxide groups changes the structural organization of DTmBDT and induces the emergence of PTs. This knowledge may facilitate crystal engineering of π‐stacked paramagnets and related molecular spin devices.

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Alternating Copolymers Incorporating Dithienogemolodithiophene for Field-Effect Transistor Applications

Abstract: 10.04.15 KB. Ok to add published OA paper to spira

Cited by 23 publications

References 54 publications

Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications

Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications

Intramolecular Energy Transfer in Dithienogermole Derivatives

The Design of Radical Stacks: Nitronyl‐Nitroxide‐Substituted Heteropentacenes

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