Synthesis, photophysical, electrochemical and single-crystal x-ray diffraction study of (<i>Z</i>)-2-phenyl-3-(5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)acrylonitrile

Bhanvadia, Viraj J.; Patel, Heta A.; Sharma, Neha; Patel, Arun L.

doi:10.1080/00397911.2016.1185125

Cited by 5 publications

(2 citation statements)

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“…Phenyl-C 61 -butyric acid methyl ester (PC 61 BM) and phenyl-C 71 -butyric acid methyl ester (PC 71 BM) were purchased from American Dye Source. N,N -Diethyl-3-thiophenecarboxamide ( 1 ), benzo[1,2- b :4,5- b ′]dithiophene-4,8-dione ( 2 ), benzo[1,2- b :4,5- b ′]dithiophene-4,8-bis[2-[triisopropylsilyl]ethynyl] ( 3 ), 2,6-dibromo-4,8-bis[2-[triisopropylsilyl]ethynyl] ( 4 ), trans -chloro(phenylethynyl)bis(tributylphosphine)platinum ( 7 ), 4,7-di-2-thienyl-2,1,3-benzothiadiazole ( 9 ), 5-[7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl]-2-thiophenecarboxaldehyde ( 10 ), and 5-[7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl]-2-thiophenemethanol ( 11 ) were synthesized according to literature procedures. The 300.13 MHz 1 H, 75.48 MHz 13 C, 121.5 MHz 31 P spectra were recorded on a Bruker Avance III Solution 300 spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…(4), 12 transchloro(phenylethynyl)bis(bributylphosphine)platinum(7), 13 4,7-di-2-thienyl-2,1,3-benzothiadiazole (9), 14 5-[7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl]-2-thiophenecarboxaldehyde (10), 15 5-[7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl]-2thiophenemethanol (11), 16 were synthesized according to literature procedures. 300.13 MHz 1 H, 75.48 MHz 13 C, 121.5 MHz 31 P spectra were recorded on a Bruker Avance III Solution 300 spectrometer.…”

Section: Introductionmentioning

confidence: 99%

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“Roller-Wheel”-Type Pt-Containing Small Molecules and the Impact of “Rollers” on Material Crystallinity, Electronic Properties, and Solar Cell Performance

Livshits

Dickie

et al. 2017

J. Am. Chem. Soc.

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We report the synthesis, characterization, and detailed comparison of a series of novel Pt-bisacetylide containing conjugated small molecules possessing an unconventional "roller-wheel" shaped structure that is distinctly different from the "dumbbell" designs in traditional Pt-bisacetylide containing conjugated polymers and small molecules. The relationships between the chemical nature and length of the "rollers" and the electronic and physical properties of the materials are carefully studied by steady-state spectroscopy, cyclic voltammetry, differential scanning calorimetry, single-crystal X-ray diffraction, transient absorption spectroscopy, theoretical calculation, and device application. It was revealed that if the roller are long enough, these molecules can "slip-stack" in the solid state, leading to high crystallinity and charge mobility. Organic solar cells were fabricated and showed power conversion efficiencies up to 5.9%, out-performing all existing Pt-containing materials. The device performance was also found to be sensitive to optimization conditions and blend morphologies, which are a result of the intricate interplay among materials crystallinity, phase separation, and the relative positions of the lowest singlet and triplet excited states.

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