Forming a three-dimensional porous organic network via solid-state explosion of organic single crystals

• Published in: Nature communications Vol. 8; no. 1; pp. 1599 - 7
• Main Authors: Bae, Seo-Yoon, Kim, Dongwook, Shin, Dongbin, Mahmood, Javeed, Jeon, In-Yup, Jung, Sun-Min, Shin, Sun-Hee, Kim, Seok-Jin, Park, Noejung, Lah, Myoung Soo, Baek, Jong-Beom
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 17.11.2017; Nature Publishing Group; Nature Portfolio
• Subjects: 639/301/357/551; 639/638/298/923/3931; 639/925/357/551; Calorimetry; Crystal lattices; Crystals; Density functional theory; Differential scanning calorimetry; Explosions; Humanities and Social Sciences; Manufacturing industry; multidisciplinary; Organic chemistry; Science; Science (multidisciplinary); Single crystals; Solid state; Staggering; X-ray diffraction
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-017-01568-3

Solid-state reaction of organic molecules holds a considerable advantage over liquid-phase processes in the manufacturing industry. However, the research progress in exploring this benefit is largely staggering, which leaves few liquid-phase systems to work with. Here, we show a synthetic protocol for the formation of a three-dimensional porous organic network via solid-state explosion of organic single crystals. The explosive reaction is realized by the Bergman reaction (cycloaromatization) of three enediyne groups on 2,3,6,7,14,15-hexaethynyl-9,10-dihydro-9,10-[1,2]benzenoanthracene. The origin of the explosion is systematically studied using single-crystal X-ray diffraction and differential scanning calorimetry, along with high-speed camera and density functional theory calculations. The results suggest that the solid-state explosion is triggered by an abrupt change in lattice energy induced by release of primer molecules in the 2,3,6,7,14,15-hexaethynyl-9,10-dihydro-9,10-[1,2]benzenoanthracene crystal lattice. Porous organic networks are of great fundamental and technological interest. Here, the authors synthesize a three-dimensional porous organic network with high specific surface area via a solid-state explosive reaction of hexaethynyl triptycene single crystals containing primer molecules.