Engineering the solid-state luminescence of organic crystals and cocrystals

Abstract

A crystal engineering approach has been used to investigate the integrated impact of functionalization and co-crystallization on the photophysical properties of organic solids.

Novel Salts of Heterocyclic Polyamines and 5-Sulfosalicylic Acid: Synthesis, Crystal Structure, and Hierarchical Supramolecular Interactions

“…In summary, a series of novel salts of heterocyclic polyamines with 5-sulfosalicylic acid, namely 2,4-diaminopyrimidin-1-ium 3-carboxy-4-hydroxybenzenesulfonate dihydrate (1), 2,4-diamino-6-chloropyrimidin-1-ium 3-carboxy-4-hydroxybenzenesulfonate hydrate (2), 2,6-diaminopyridin-1-ium 3-carboxy-4-hydroxybenzenesulfonate monohydrate (3), 2,6diamino-9H-purin-1-ium 3-carboxy-4-hydroxybenzenesulfonate monohydrate (4), and 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 3-carboxy-4-hydroxybenzenesulfonate (6) have been reported for the first time, to the best of our knowledge. We managed to successfully synthesize and crystallize new salts and determine their crystal structures by single-crystal X-ray diffraction.…”

“…Organic salts based on 2-hydroxy-5-sulfobenzoic (5-sulfosalicylic) acid are eagerly studied due to their interesting optical and pharmaceutical properties [1][2][3][4][5][6]. Many salts, including one negative 3-carboxy-4-hydroxybenzenesulfonate anion, C 7 H 5 O 6 S − (with a negative charge at the sulfonyl group), have been presented.…”

Stimuli-responsive fluorochromic organic salt

“…12,43,51 Recently, we realized solid-state emission tuning in organic complexes based on ionic interactions. [39][40][41] Although common in charge transfer co-crystals, solid-state emission, and its tuning have rarely been reported for hydrogen-bonded co-crystals or salts. 37,52 Only a few instances of the realization of emission tuning in hydrogen-bonded binary crystal systems involve solvates.…”

“…38 Similarly, Yang and Gazit have demonstrated that hydrogen bonding interactions can lead to emission tuning in the host-guest crystals of 1-(5-(anthracen-9-yl)-3-(4-methoxyphenyl)-4,5-dihydropyrazol-1-yl)ethenone. 39 Notably, we have reported the realization of conformer-dependent emission tuning as well as ''on-off'' switching in hydrogen-bonded ionic cocrystals. [40][41][42] Although less reported, their being predominantly kinetic solid forms and the presence of an acidic hydrogen in the hydrogenbonded emissive crystal structures makes them suitable candidates for the investigation of stimuli-responsive behavior.…”

Photoluminescent organic crystals and co-crystals

“…169 The combined impact of functionalization and co-crystallization was employed to explore emission tuning in sulfonate-pyridiniumbased organic salts. 170 However, emission engineering through hydrogen bonds is random, and based on the available literature, reliable design strategies cannot be established.…”