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Keller, Niklas; Bessinger, Derya; Reuter, Stephan; Calik, Mona; Ascherl, Laura; Hanusch, Fabian C.; Auras, Florian; Bein, Thomas (2017): Oligothiophene-Bridged Conjugated Covalent Organic Frameworks. In: Journal of the American Chemical Society, Vol. 139, No. 24: pp. 8194-8199
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Two-dimensional covalent organic frameworks (2D-COFs) are crystalline, porous materials comprising aligned columns of pi-stacked building blocks. With a-view toward the application of these materials in organic electronics and optoelectronics, the construction of oligothiophene-based COFs would be highly desirable. The realization of such materials, however, has remained a challenge, in particular with respect to laterally conjugated imine-linked COFs. We have developed a new building block design employing an asymmetric modification on an otherwise symmetric backbone that allows us to construct a series of highly crystalline quaterthiophene-derived COFs with tunable electronic properties. Studying the optical response of these materials, we have observed for the first time the formation of a charge transfer state between the COF subunits across the imine bond. We believe that our new building block design provides a general strategy for the construction of well-ordered COFs from various extended building blocks, thus greatly expanding the range of applicable molecules.