Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Predictably Ordered Open Hydrogen-Bonded Networks Built from Indeno[1,2-b]fluorenes

Predictably Ordered Open Hydrogen-Bonded Networks Built from Indeno[1,2-b]fluorenes
Joao-Nicolas Blair-Pereira, Sophie Langis-Barsetti, Daniel Beaudoin, James D. Wuest, Thierry Maris
Predictably ordered materials can be constructed by a modular strategy in which properly designed molecular components are positioned in space by reliable interactions. In principle, this approach can be used to control the arrangement of adjacent systems of π-conjugation, thereby creating molecular materials with valuable optoelectronic properties. To explore this possibility, we have synthesized compounds in which 2,4-diamino-1,3,5-triazinyl groups are attached to derivatives of 6,12-dihydroindeno[1,2-b]fluorene to produce molecules with well-defined cruciform topologies, extended π-conjugated aromatic cores, and an ability to form multiple hydrogen bonds. These compounds crystallize to form robust open hydrogen-bonded networks with parallel indenofluorenyl cores, significant volume (64–70%) available for accommodating guests, and characteristic luminescence. Our results will help permit the rational design of complex new molecular materials in which multiple optoelectronically active components are arranged in productive ways.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01333

DOI: 10.1021/acs.joc.7b01333

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