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2,1,3-Benzothiadiazole-5,6-dicarboxylic imide--a versatile building block for additive- and annealing-free processing of organic solar cells with efficiencies exceeding 8%.

ABSTRACT: A new photoactive polymer comprising benzo[1,2-b:3,4-b':5,6-d']trithiophene and 2,1,3-benzothiadiazole-5,6-dicarboxylic imide is reported. The synthetic design allows for alkyl chains to be introduced on both electron-rich and electron-deficient components, which in turn allows for rapid optimization of the alkyl chain substitution pattern. Consequently, the optimized polymer shows a maximum efficiency of 8.3% in organic photovoltaic devices processed in a commercially viable fashion without solvent additives, annealing, or device engineering.

SUBMITTER: Nielsen CB

PROVIDER: S-EPMC4365755 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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2,1,3-Benzothiadiazole-5,6-dicarboxylic imide--a versatile building block for additive- and annealing-free processing of organic solar cells with efficiencies exceeding 8%.

Nielsen Christian B CB Ashraf Raja Shahid RS Treat Neil D ND Schroeder Bob C BC Donaghey Jenny E JE White Andrew J P AJ Stingelin Natalie N McCulloch Iain I

Advanced materials (Deerfield Beach, Fla.) 20141215 5

A new photoactive polymer comprising benzo[1,2-b:3,4-b':5,6-d']trithiophene and 2,1,3-benzothiadiazole-5,6-dicarboxylic imide is reported. The synthetic design allows for alkyl chains to be introduced on both electron-rich and electron-deficient components, which in turn allows for rapid optimization of the alkyl chain substitution pattern. Consequently, the optimized polymer shows a maximum efficiency of 8.3% in organic photovoltaic devices processed in a commercially viable fashion without sol ...[more]

PMID: 25511684

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Project description:A two-photon absorbing (2PA) red emitter group was chemically conjugated onto amphiphilic poly(ethylene glycol)-block-poly(ε-caprolactone) (PEG-b-PCL) copolymers, and further grafted with cyclo (Arg-Gly-Asp) (cRGD) peptide to form micelle 1. Micelle 1 with cRGD targeting groups were used for targeted bioimaging. For comparison, micelle 2 without the cRGD targeting groups were also prepared and investigated. The micelles were characterized using dynamic light scattering (DLS), showing average diameters of around 77 nm. The cRGD targeting group is known to bind specifically with α v β 3 integrin in cancer cells. In this study, α v β 3 integrin overexpressed human glioblastoma U87MG cell line and α v β 3 integrin deficient human cervical cancer HeLa cell line were chosen. Results showed that the cRGD targeting group enhanced the cellular uptake efficiency of the micelles significantly in α v β 3 integrin rich U87MG cells. Higher temperature (37 °C versus 4 °C) and calcium ions (with 3M calcium chloride in the cell culture medium versus no addition of calcium ions) enhanced the cellular uptake efficiency, suggesting that the uptake of the micelles is through the endocytosis pathway in cells. A 3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) viability assay was used to evaluate the cytotoxicity of the micelles and no significant cytotoxicity was observed. The BTD-containing two-photon absorbing emitter in the micelles showed a two-photon absorbing cross-section of 236 GM (1GM = 1 × 10-50 cm4 s photon-1 molecule-1) at 820 nm, which is among the highest values reported for red 2PA emitters. Because of the two-photon absorbing characteristics, micelle 1 was successfully used for two-photon fluorescence imaging targeted to U87MG cells under a two-photon fluorescence microscope. This study is the first report regarding the targeted imaging of a specific cancer cell line (herein, U87MG) using the BTD-conjugated-fluorophore-containing block copolymers.

Dataset Information

2,1,3-Benzothiadiazole-5,6-dicarboxylic imide--a versatile building block for additive- and annealing-free processing of organic solar cells with efficiencies exceeding 8%.

Publications

2,1,3-Benzothiadiazole-5,6-dicarboxylic imide--a versatile building block for additive- and annealing-free processing of organic solar cells with efficiencies exceeding 8%.

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