Engineering the Solid State with 2-Benzimidazolones

Abstract

Six derivatives of 2-benzimidazolone, disubstituted in the 4 and 5 positions, have been synthesized, and their structures have been determined in the solid state. Four of these compounds crystallize as molecular tapes. Compounds 1-(CH3)2 , 1-Cl2 , and 1-Br2 form tapes that pack with their long axes parallel; compounds 1-H2 and 2-H2 form tapes that pack with their long axes at an angle to one another. Compounds 1-F2 and 1-I2 crystallize with a three-dimensional network of hydrogen bonds. The packing arrangement of molecular tapes is rationalized on the basis of closest packing and electrostatic interactions between aromatic rings. The occurrence of the network motif rather than the tape motif for 1-F2 and 1-I2 is rationalized on the basis of secondary interactions involving the halogen atoms.

Packing Modes in Nitrobenzene Derivatives. II. The `Pseudo-Herringbone' Mode

“…The successive substitution of these nitrobenzene derivatives seems to affect their mode of packing going from 'pseudo-herringbone' patterns to stacks, with totally substituted nitrobenzene derivatives (except DOHCUY) forming stacks. In a similar way, the influence of substitution on planar benzimidazolones has been observed (Schwiebert, Chin, MacDonald & Whitesides, 1996) and the mode of packing of these compounds has been shown to be drastically affected by the substitution due to a change in the shape of the benzimidazolone molecules. Furthermore, a homology in the mode of packing of the 1,3,5-trinitrobenzene derivatives (SAWBIB, CLNOBE02, DCTNBZ and TNOXYL) is observed.…”

Beyond molecules: Self-assembly of mesoscopic and macroscopic components

“…The cell contains an astonishing range of complex structures such as lipid membranes, folded proteins, structured nucleic acids, protein aggregates, molecular machines, and many others that form by self-assembly (12). The second is that self-assembly provides routes to a range of materials with regular structures: molecular crystals (13), liquid crystals (14), and semicrystalline and phase-separated polymers (15) are examples. Third, self-assembly also occurs widely in systems of components larger than molecules, and there is great potential for its use in materials and condensed matter science (16).…”

Resorcinarenes with 2-benzimidazolone bridges: Self-aggregation, self-assembled dimeric capsules, and guest encapsulation

“…1). Alternatively, cyclic ureas, such as 2-benzimidazolone, interact in a geometrically more efficient way by using hydrogen donors from two different urea functions (8,9). This result prompted us to design self-assembling resorcinarenes 1 bridged by four cyclic ureas.…”