Structure and photoconductive behavior of (E-) and (Z-)-1-cyano-1-carbethoxymethylene acenaphthen-2-one taken by stereoselective synthesis

Mhaidat, I; Hamilakis, S; Kollia, C; Tsolomitis, A; Loizos, Z

dc.contributor.author	Mhaidat, I	en
dc.contributor.author	Hamilakis, S	en
dc.contributor.author	Kollia, C	en
dc.contributor.author	Tsolomitis, A	en
dc.contributor.author	Loizos, Z	en
dc.date.accessioned	2014-03-01T01:27:19Z
dc.date.available	2014-03-01T01:27:19Z
dc.date.issued	2007	en
dc.identifier.issn	0167-577X	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/18397
dc.subject	π-conjugated system	en
dc.subject	Electronic material	en
dc.subject	Photoconduction	en
dc.subject	Photocurrent	en
dc.subject	Small-molecule organic semiconductor	en
dc.subject	Stereoselective synthesis	en
dc.subject.classification	Materials Science, Multidisciplinary	en
dc.subject.classification	Physics, Applied	en
dc.subject.other	Condensation	en
dc.subject.other	Hydrogen bonds	en
dc.subject.other	Infrared spectroscopy	en
dc.subject.other	Ketones	en
dc.subject.other	Molecular structure	en
dc.subject.other	Nuclear magnetic resonance spectroscopy	en
dc.subject.other	Photoconductivity	en
dc.subject.other	Photocurrents	en
dc.subject.other	Photoelectrochemical cells	en
dc.subject.other	Semiconducting organic compounds	en
dc.subject.other	X ray diffraction	en
dc.subject.other	Electronic materials	en
dc.subject.other	Photoconduction	en
dc.subject.other	Stereoselective synthesis	en
dc.subject.other	Z-diastereomers	en
dc.subject.other	Aromatic compounds	en
dc.title	Structure and photoconductive behavior of (E-) and (Z-)-1-cyano-1-carbethoxymethylene acenaphthen-2-one taken by stereoselective synthesis	en
heal.type	journalArticle	en
heal.identifier.primary	10.1016/j.matlet.2006.04.056	en
heal.identifier.secondary	http://dx.doi.org/10.1016/j.matlet.2006.04.056	en
heal.language	English	en
heal.publicationDate	2007	en
heal.abstract	The stereoselective synthesis of the two geometric isomers (E-) and (Z-) of 1-cyano-1-carbethoxymethylene acenaphthen-2-one, was achieved via two different, simple, pure and low cost Knovenagel condensation reactions. The chemical structure of the as-prepared isomers was identified by H-1 NMR technique, IR spectroscopy, elemental analysis and X-ray diffraction. Photoconductivity measurements of both the isomers isolated and formulated as thin films on titanium substrates were performed by a solution deposition technique in a photoelectrochemical cell (PEC) under different illumination conditions. The photocurrents observed might be attributed to the structure of the substances prepared which favors the development of an extended pi-conjugated system. However, the Z-isomer presents higher photoconductivity compared with that of the E-isomer. So, it could be supposed that the lower photoresponse characterizing the E-isomer is due to an observed development of a non-traditional intramolecular hydrogen bond leading to the formation of an additional six-membered ring. The Z-diastereomer, belonging to the group of small-molecule semiconductors, may be useful in devices as organic thin film transistors, on/off sensors, etc. (c) 2006 Elsevier B.V. All rights reserved.	en
heal.publisher	ELSEVIER SCIENCE BV	en
heal.journalName	Materials Letters	en
dc.identifier.doi	10.1016/j.matlet.2006.04.056	en
dc.identifier.isi	ISI:000243253800005	en
dc.identifier.volume	61	en
dc.identifier.issue	2	en
dc.identifier.spage	321	en
dc.identifier.epage	325	en