Novel naphtho[1,2-b:5,6-b′]dithiophene core linear donor–π–acceptor conjugated small molecules with thiophene-bridged bithiazole acceptor: design, synthesis, and their application in bulk heterojunction organic solar cells

Dutta, Pranabesh; Yang, Wooseung; Lee, Woo Hyung; Kang, In Man; Lee, Soo-Hyoung

doi:10.1039/c2jm30934c

Cited by 37 publications

(19 citation statements)

References 102 publications

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“…Two typical broad diffraction peaks are observed in all these thin films. The first [43,44]. The shortest inter-chain spacing and stacking distance are found in the PBDTT-BTQ thin film, which is consistent with its highest hole mobility.…”

Section: Hole Mobilitysupporting

confidence: 67%

Manipulating backbone structure with various conjugated spacers to enhance photovoltaic performance of D–A-type two-dimensional copolymers

Dang

Xiao

Zhou

et al. 2014

Organic Electronics

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a b s t r a c tA class of low band-gap two-dimensional conjugated polymers of PBDTT-FQ, PBDTT-TQ, PBDTT-BTQ and PBDTT-TTQ was designed and synthesized, which contains the same di(alkylthiophene)-substituted benzo [1,2-b:4,5-b 0 ]dithiophene (BDTT) and 6,7-difluoroquinoxaline (Q) units, as well as various conjugated spacers of furan, thiophene, bithiophene and thieno [3,2-b]thiophene in the main chain. Significant effect of the varied spacers between the BDTT and Q units on the thermal, optical, electrochemical and photovoltaic properties was investigated and observed for these two-dimensional copolymers in the polymer solar cells. The maximum power conversion efficiency of 5.9% with a short circuit current of 13.7 mA/cm 2 and a fill factor of 0.56 was obtained for the PBDTT-TQ with thiophene spacer in the bulk hetero-junction PSCs using [6,6]-phenyl-C 71 -butyric acid methyl ester as acceptor.

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Section: Hole Mobilitysupporting

confidence: 67%

Manipulating backbone structure with various conjugated spacers to enhance photovoltaic performance of D–A-type two-dimensional copolymers

Dang

Xiao

Zhou

et al. 2014

Organic Electronics

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“…In 2012, Lee and co‐workers explored the possibility of using thiazole‐containing small molecules as an active material in thin‐film devices. M11 and M12 were synthesized via stepwise Pd‐catalyzed Suzuki and Stille coupling reactions . The π‐conjugated organic small molecule M11 contains a rigid fused naphtha dithiophene core flanked by a bithiazole, whereas M12 contains a triphenylamine‐capped thiophene(3‐decanyl)‐bridged bithiazole.…”

Section: Bithiazole‐based Small Moleculesmentioning

confidence: 99%

Bithiazole: An Intriguing Electron‐Deficient Building for Plastic Electronic Applications

Sredojević

Bronstein

et al. 2017

Macromol. Rapid Commun.

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The heterocyclic thiazole unit has been extensively used as electron-deficient building block in π-conjugated materials over the last decade. Its incorporation into organic semiconducting materials is particularly interesting due to its structural resemblance to the more commonly used thiophene building block, thus allowing the optoelectronic properties of a material to be tuned without significantly perturbing its molecular structure. Here, we discuss the structural differences between thiazole- and thiophene-based organic semiconductors, and the effects on the physical properties of the materials. An overview of thiazole-based polymers is provided, which have emerged over the past decade for organic electronic applications and it is discussed how the incorporation of thiazole has affected the device performance of organic solar cells and organic field-effect transistors. Finally, in conclusion, an outlook is presented on how thiazole-based polymers can be incorporated into all-electron deficient polymers in order to obtain high-performance acceptor polymers for use in bulk-heterojunction solar cells and as organic field-effect transistors. Computational methods are used to discuss some newly designed acceptor building blocks that have the potential to be polymerized with a fused bithiazole moiety, hence propelling the advancement of air-stable n-type organic semiconductors.

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“…A sufficiently longer conjugation bridge like thiophene [22][23][24], oligothiophene derivatives [25,26] or fused-thiophene provides an extension of the absorption towards the red and NIR wavelengths as well as an increase of the absorption coefficient due to strong intramolecular charge transfer (ICT). More detailed discussion on π-bridge of thiophene and its derivatives are depicted in the following part.…”

Section: π-Linkage With Thiophene and Its Derivativesmentioning

confidence: 99%

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

Yin

2016

Sci. China Mater.

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Much attention has been paid to the push-pullstructure organic small molecule (OSM) materials for photovoltaic (PV) application in the past decade, due to their facile reduction of energy band gap (Eg) and effective control of PV properties. π-bridge plays an important role in the push-pull-structure OSMs since an appropriate π-linkage is crucial for improving the PV performance of organic solar cells (OSCs). In this review, various π-bridge groups (thiophene, alkene, alkyne, arene and heterocycle) and the pertinent π-linkage effect will be systematically summarized. These results suggest that the in-depth study of the π-linkage effect is essential to deeply understanding the relationship between the molecular structure and property, thus improving PV performance.

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Novel naphtho[1,2-b:5,6-b′]dithiophene core linear donor–π–acceptor conjugated small molecules with thiophene-bridged bithiazole acceptor: design, synthesis, and their application in bulk heterojunction organic solar cells

Cited by 37 publications

References 102 publications

Manipulating backbone structure with various conjugated spacers to enhance photovoltaic performance of D–A-type two-dimensional copolymers

Manipulating backbone structure with various conjugated spacers to enhance photovoltaic performance of D–A-type two-dimensional copolymers

Bithiazole: An Intriguing Electron‐Deficient Building for Plastic Electronic Applications

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

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