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Dehydrative ?-extension to nanographenes with zig-zag edges.

ABSTRACT: Zig-zag nanographenes are promising candidates for the applications in organic electronics due to the electronic properties induced by their periphery. However, the synthetic access to these compounds remains virtually unexplored. There is a lack in efficient and mild strategies origins in the reduced stability, increased reactivity, and low solubility of these compounds. Herein we report a facile access to pristine zig-zag nanographenes, utilizing an acid-promoted intramolecular reductive cyclization of arylaldehydes, and demonstrate a three-step route to nanographenes constituted of angularly fused tetracenes or pentacenes. The mild conditions are scalable to gram quantities and give insoluble nanostructures in close to quantitative yields. The strategy allows the synthesis of elusive low bandgap nanographenes, with values as low as 1.62?eV. Compared to their linear homologues, the structures have an increased stability in the solid-state, even though computational analyses show distinct diradical character. The structures were confirmed by X-ray diffraction or scanning tunneling microscopy.

SUBMITTER: Lungerich D

PROVIDER: S-EPMC6232111 | biostudies-other | 2018 Nov

REPOSITORIES: biostudies-other

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Dehydrative π-extension to nanographenes with zig-zag edges.

Lungerich Dominik D Papaianina Olena O Feofanov Mikhail M Liu Jia J Devarajulu Mirunalini M Troyanov Sergey I SI Maier Sabine S Amsharov Konstantin K

Nature communications 20181112 1

Zig-zag nanographenes are promising candidates for the applications in organic electronics due to the electronic properties induced by their periphery. However, the synthetic access to these compounds remains virtually unexplored. There is a lack in efficient and mild strategies origins in the reduced stability, increased reactivity, and low solubility of these compounds. Herein we report a facile access to pristine zig-zag nanographenes, utilizing an acid-promoted intramolecular reductive cycli ...[more]

PMID: 30420660

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Project description:Purpose(1) To devise a model-based method for estimating the probabilities of binocular fusion, interocular suppression and diplopia from psychophysical judgements, (2) To map out the way fusion, suppression and diplopia vary with binocular disparity and blur of single edges shown to each eye, (3) To compare the binocular interactions found for edges of the same vs opposite contrast polarity.MethodsTest images were single, horizontal, Gaussian-blurred edges, with blur B = 1-32 min arc, and vertical disparity 0-8.B, shown for 200 ms. In the main experiment, observers reported whether they saw one central edge, one offset edge, or two edges. We argue that the relation between these three response categories and the three perceptual states (fusion, suppression, diplopia) is indirect and likely to be distorted by positional noise and criterion effects, and so we developed a descriptive, probabilistic model to estimate both the perceptual states and the noise/criterion parameters from the data.Results(1) Using simulated data, we validated the model-based method by showing that it recovered fairly accurately the disparity ranges for fusion and suppression, (2) The disparity range for fusion (Panum's limit) increased greatly with blur, in line with previous studies. The disparity range for suppression was similar to the fusion limit at large blurs, but two or three times the fusion limit at small blurs. This meant that diplopia was much more prevalent at larger blurs, (3) Diplopia was much more frequent when the two edges had opposite contrast polarity. A formal comparison of models indicated that fusion occurs for same, but not opposite, polarities. Probability of suppression was greater for unequal contrasts, and it was always the lower-contrast edge that was suppressed.ConclusionsOur model-based data analysis offers a useful tool for probing binocular fusion and suppression psychophysically. The disparity range for fusion increased with edge blur but fell short of complete scale-invariance. The disparity range for suppression also increased with blur but was not close to scale-invariance. Single vision occurs through fusion, but also beyond the fusion range, through suppression. Thus suppression can serve as a mechanism for extending single vision to larger disparities, but mainly for sharper edges where the fusion range is small (5-10 min arc). For large blurs the fusion range is so much larger that no such extension may be needed.

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Dehydrative ?-extension to nanographenes with zig-zag edges.

Publications

Dehydrative π-extension to nanographenes with zig-zag edges.

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