Predictably Ordered Open Hydrogen-Bonded Networks Built from Indeno[1,2‑<i>b</i>]fluorenes

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.