Molecular-shape-controlled photovoltaic performance probed via soluble π-conjugated arylacetylenic semiconductors.

The synthesis and characterization of a new series of anthracene-based derivatives and their use as donors in bulk-heterojunction solar cells is reported. It is found that when using well-defined building blocks in constructing the chromophore, the donor molecular shape dramatically affects organic photovoltaic (OPV) performance in a previously unrecognized way.

Solution-processable low-molecular weight extended arylacetylenes: versatile p-type semiconductors for field-effect transistors and bulk heterojunction solar cells.

We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl}phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-benzothiadiazole (TBTZ-P6t, 6), and 7,7'-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4'-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OPV) cells fabricated. We find that substituting acetylenic for olefinic linkers on the molecular cores significantly enhances device performance. OFET measurements reveal that all seven of the semiconductors are FET-active and, depending on the backbone architecture, the arylacetylenes exhibit good p-type mobilities (mu up to approximately 0.1 cm(2) V(-1) s(-1)) when optimum film microstructural order is achieved. OPV cells using [6,6]-phenyl C(61)-butyric acid methyl ester (PCBM) as the electron acceptor exhibit power conversion efficiencies (PCEs) up to 1.3% under a simulated AM 1.5 solar irradiation of 100 mW/cm(2). These results demonstrate that arylacetylenes are promising hole-transport materials for p-channel OFETs and promising donors for organic solar cells applications. A direct correlation between OFET arylacetylene hole mobility and OPV performance is identified and analyzed.

Conjugated anthracene derivatives as donor materials for bulk heterojunction solar cells: olefinic versus acetylenic spacers.

Substituting olefinic for acetylenic pi-spacers in anthracene-based conjugated semiconductor donors leads to appreciable increases in the power conversion efficiencies of the resulting bulk heterojunction solar cells.

Quantitative structure-activity relationship modeling of polycyclic aromatic hydrocarbon mutagenicity by classification methods based on holistic theoretical molecular descriptors.

Various polycyclic aromatic hydrocarbons (PAHs), ubiquitous environmental pollutants, are recognized mutagens and carcinogens. A homogeneous set of mutagenicity data (TA98 and TA100,+S9) for 32 benzocyclopentaphenanthrenes/chrysenes was modeled by the quantitative structure-activity relationship classification methods k-nearest neighbor and classification and regression tree, using theoretical holistic molecular descriptors. Genetic algorithm provided the selection of the best subset of variables for modeling mutagenicity. The models were validated by leave-one-out and leave-50%-out approaches and have good performance, with sensitivity and specificity ranges of 90-100%. Mutagenicity assessment for these PAHs requires only a few theoretical descriptors of their molecular structure.