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1.
Org Lett ; 16(10): 2642-5, 2014 May 16.
Article in English | MEDLINE | ID: mdl-24796375

ABSTRACT

New acceptor-donor-acceptor (A-D-A) oligomers (1 and 2) containing a central dithieno[3,2-b:2',3'-d]pyrrole unit and end-capping thieno[2,3-c]pyrrole-4,6-dione groups have been synthesized and characterized. Bulk heterojunction solar cells were prepared together with PC61BM and PC71BM, and the best results were obtained for the latter acceptor using 1,8-diiodooctane as an additive. Photovoltaic devices containing these oligomers achieved high external quantum efficiencies up to 50%.

2.
Beilstein J Nanotechnol ; 4: 680-9, 2013.
Article in English | MEDLINE | ID: mdl-24205464

ABSTRACT

The optimization of solution-processed organic bulk-heterojunction solar cells with the acceptor-substituted quinquethiophene DCV5T-Bu 4 as donor in conjunction with PC61BM as acceptor is described. Power conversion efficiencies up to 3.0% and external quantum efficiencies up to 40% were obtained through the use of 1-chloronaphthalene as solvent additive in the fabrication of the photovoltaic devices. Furthermore, atomic force microscopy investigations of the photoactive layer gave insight into the distribution of donor and acceptor within the blend. The unique combination of solubility and thermal stability of DCV5T-Bu 4 also allows for fabrication of organic solar cells by vacuum deposition. Thus, we were able to perform a rare comparison of the device characteristics of the solution-processed DCV5T-Bu 4 :PC61BM solar cell with its vacuum-processed DCV5T-Bu 4 :C60 counterpart. Interestingly in this case, the efficiencies of the small-molecule organic solar cells prepared by using solution techniques are approaching those fabricated by using vacuum technology. This result is significant as vacuum-processed devices typically display much better performances in photovoltaic cells.

3.
Chem Commun (Camb) ; 49(92): 10865-7, 2013 Nov 28.
Article in English | MEDLINE | ID: mdl-24126293

ABSTRACT

Isomeric dicyanovinylene-terminated oligothiophenes 1 and 2 comprising a central dithienopyrrole (DTP) unit have been developed for solution-processed small molecule organic solar cells (SMOSCs) giving the highest power conversion efficiency of 4.8% for DTP-based oligomeric materials.

4.
Chemistry ; 18(40): 12880-901, 2012 Oct 01.
Article in English | MEDLINE | ID: mdl-22907912

ABSTRACT

The synthesis of generational dendritic oligothiophenes (DOTs) has been successfully achieved by a divergent/convergent approach that involves halogenation, boronation, and palladium-catalyzed Suzuki coupling reactions. The key point in the presented synthetic approach is the use of trimethylsilyl (TMS) protecting groups, which allow for the core-lithiation and subsequent boronation of the dendrons and for the peripheral ipso-substitution with iodine monochloride or N-bromosuccimide. In addition, the TMS protecting groups can be completely removed by using tetrabutylammonium fluoride, thus yielding only-thiophene-based dendrons and dendrimers. Due to their highly branched structure, all these synthesized DOTs are soluble in organic solvents. Chemical structures were confirmed by NMR spectroscopic, mass spectrometric, and elemental analysis. Concentration-dependent (1)H NMR spectroscopic investigations revealed that the higher generation compounds tend to aggregate in solution. Such an aggregation behavior was further confirmed by measuring with MALDI-TOF MS. Both MALDI-TOF MS and gel-permeation chromatography (GPC) analyses confirmed the monodispersity of the DOTs. Furthermore, GPC results revealed that these DOT molecules adopt a condensed globular molecular shape. Their optical and electronic properties were also investigated. The results indicated that these DOTs comprise various conjugated α-oligothiophenes with different chain lengths, which results in the higher generation compounds showing broad and featureless UV/Vis absorption spectra and ill-defined redox waves.

5.
J Am Chem Soc ; 134(27): 11064-7, 2012 Jul 11.
Article in English | MEDLINE | ID: mdl-22694124

ABSTRACT

The novel methyl-substituted dicyanovinyl-capped quinquethiophenes 1-3 led to highly efficient organic solar cells with power conversion efficiencies of 4.8-6.9%. X-ray analysis of single crystals and evaporated neat and blend films gave insights into the packing and morphological behavior of the novel compounds that rationalized their improved photovoltaic performance.

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