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Open Access Nonplanar Push–Pull Chromophores for Opto-Electronic Applications

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Donor-substituted cyanoethynylethenes (CEEs) are planar push–pull chromophores featuring intense intramolecular charge-transfer (CT) interactions and high third-order optical nonlinearities. Their thermal stability allows for the formation of crystalline thin films by vapor-phase deposition. On the other hand, high-quality amorphous thin films are preferred for opto-electronic applications and such films can be prepared using nonplanar push–pull chromophores with a less pronounced propensity to crystallize. By taking advantage of a versatile, atom-economic 'click-chemistry'-type transformation, involving a formal [2 + 2] cycloaddition of tetracyanoethene (TCNE) to electron-rich alkynes, followed by cycloreversion, stable donor-substituted 1,1,4,4-tetracyanobuta-1,3-dienes (TCBDs) are obtained in high yield and large quantities. These nonplanar push–pull chromophores also feature intense intramolecular CT and, in many cases, high third-order optical nonlinearities. Some of these compounds form high-optical-quality amorphous thin films by vapor-phase deposition, and first applications in next-generation opto-electronic devices have already been demonstrated. Chiral derivatives display high helical twisting power and are efficient dopants to translate molecular into macroscopic chirality, by switching nematic into cholesteric liquid crystalline phases.

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Keywords: ALKYNES; CHARGE-TRANSFER; CYCLOADDITION; DONOR-ACCEPTOR SYSTEMS; NONLINEAR OPTICS

Document Type: Research Article

Affiliations: 1: Laboratorium für Organische Chemie der, Eidgenössischen Technischen Hochschule, Hönggerberg, HCI, CH-8093Zürich 2: Lehigh University, Department of Physics and Center for Optical Technologies, 16 Memorial Dr. East, Bethlehem, PA 18015, USA

Publication date: June 1, 2010

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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