New Fused Bis-Thienobenzothienothiophene Copolymers and Their Use in Organic Solar Cells and Transistors

Biniek, Laure; Schroeder, Bob C.; Donaghey, Jenny E.; Yaacobi‐Gross, Nir; Ashraf, Raja Shahid; Soon, Ying Woan; Nielsen, Christian B.; Durrant, James R.; Anthopoulos, Thomas D.; McCulloch, Iain

doi:10.1021/ma302390z

Cited by 44 publications

(38 citation statements)

References 22 publications

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“…The former two properties are associated with the short circuit current ( J sc ) and partly controlled by processing conditions (solvent, additive, and thermal annealing). In one of the most common design strategies for low‐bandgap polymers, the intramolecular charge‐transfer phenomenon is rationally utilized through the alternating arrangement of donor (e.g., benzodithiophene (BDT), cychlopentadithiophene (CPDT), carbazole (Cz), fluorene (FLO)) and acceptor (e.g., benzothiadiazole (BT), thienopyrroledione (TPD), isoindigo (IIDG), diketopyrrolopyrole (DKPP)). This design allows lowering of the lowest unoccupied molecular orbital (LUMO) while keeping a deep HOMO of the copolymers.…”

Section: Introductionmentioning

confidence: 99%

Benzobisthiazole as Weak Donor for Improved Photovoltaic Performance: Microwave Conductivity Technique Assisted Molecular Engineering

Tsuji

Saeki

Koizumi

et al. 2013

Adv Funct Materials

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New donor-acceptor-type copolymers comprised of benzobisthiazole (BBTz) as a weak donor rather than acceptor are proposed. This approach can simultaneously lead to deepening the HOMO and LUMO of the polymers with moderate energy offset against fullerene derivatives in bulk heterojunction organic photovoltaics. As a proof-of-concept, BBTz-based random copolymers conjugated with typical electron acceptors: thienopyrroledione (TPD) and benzothiadiazole (BT) based on density functional theory calculations are synthesized. Laser-fl ash and Xe-fl ash time-resolved microwave conductivity (TRMC) evaluations of polymer:[6,6]-phenyl C 61 butyric acid methyl ester (PCBM) blends are conducted to screen the feasibility of the copolymers, leading to optimization of processing conditions for photovoltaic device application. According to the TMRC results, alternating BBTz-BT copolymers are designed, exhibiting extended photoabsorption up to ca. 750 nm, deep HOMO (-5.5 to -5.7 eV), good miscibility with PCBM, and inherent crystalline nature. Moreover, the maximized PCE of 3.8%, the top-class among BBTz-based polymers reported so far, is realized in an inverted cell using TiO x and MoO x as the buffer layers. This study opens up opportunities to create low-bandgap polymers with deep HOMO, and shows how the device-less TRMC evaluation is of help for decision-making on judicious molecular design.

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Section: Introductionmentioning

confidence: 99%

Benzobisthiazole as Weak Donor for Improved Photovoltaic Performance: Microwave Conductivity Technique Assisted Molecular Engineering

Tsuji

Saeki

Koizumi

et al. 2013

Adv Funct Materials

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“…Alternating copolymers were synthesized by Pdcatalyzed Stille polymerization in chlorobenzene as illustrated in Scheme 3 . [ 25 ] We copolymerized the dibrominated small molecules (17-Crown-5)T2 and (20-Crown-6)T2 with the distannylated BDT monomers [ 26 ] to afford polymers P1 and P2 with 5-ethylhexyl-2-thienyl side chains and polymers P3 and P4 with triethylene glycol side chains. Polymers P1 and P2 were obtained with respectable molecular weights ( M n = 26 kDa, M w = 73 kDa for P1 , M n = 30 kDa, M w = 44 kDa for P2 ) whereas lower molecular weights were obtained for polymers P3 and P4 ( M n = 3.2 kDa, M w = 5.6 kDa for P3 , M n = 3.6 kDa, M w = 6.0 kDa for P4 ).…”

Section: Polymerizationmentioning

confidence: 99%

Sodium and Potassium Ion Selective Conjugated Polymers for Optical Ion Detection in Solution and Solid State

Giovannitti

Nielsen

Rivnay

et al. 2015

Adv Funct Materials

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This paper presents the development of alkali metal ion selective small molecules and conjugated polymers for optical ion sensing. A crown ether bithiophene unit is chosen as the detecting unit, as both a small molecule and incorporated into a conjugated aromatic structure. The complex formation and the resulting backbone twist of the detector unit is investigated by UV-vis and NMR spectroscopy where a remarkable selectivity toward sodium or potassium ions is found. X-ray diffraction analysis of single crystals with and without alkali metal ions is carried out and a difference of the dihedral angle of more than 70° is observed. In a conjugated polymer structure, the detector unit has a higher sensitivity for alkali metal ion detection than its small molecule analog. Ion selectivity is retained in polymers with solubility in polar solvents facilitated by the attachment of polar ethylene glycol side chains. This design concept is further evolved to develop a sodium-salt solid state sensor based on blends of the detecting polymer with a polyvinyl alcohol matrix where the detection of sodium ions is achieved in aqueous salt solutions with concentrations similar to biologically important environments.

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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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New Fused Bis-Thienobenzothienothiophene Copolymers and Their Use in Organic Solar Cells and Transistors

Cited by 44 publications

References 22 publications

Benzobisthiazole as Weak Donor for Improved Photovoltaic Performance: Microwave Conductivity Technique Assisted Molecular Engineering

Benzobisthiazole as Weak Donor for Improved Photovoltaic Performance: Microwave Conductivity Technique Assisted Molecular Engineering

Sodium and Potassium Ion Selective Conjugated Polymers for Optical Ion Detection in Solution and Solid State

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

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