[structure, reaction: see text] The U-shaped, multifunctionalized tetraetheno-bridged dicyclopenta[b,i]anthracenediol 10 was synthesized to serve as a platform molecule. The molecule was prepared from the Diels-Alder adduct 5a of tricycloundecatriene 3 and bicyclo[2.2.2]octene-fused p-benzoquinone 4. Functionalization of 10 to construct crab-like molecules was achieved via the base-promoted bis-O-alkylation of two endo-oriented hydroxyl groups at termini in 10 with the following alkyl halides: allyl, propagyl, and benzyl bromides; 1-bromo- and 1-iodo-4-(bromomethyl)benzene; 9-(bromomethyl)anthracene; 1-(bromomethyl)pyrene; and isomeric bromomethylpyridines. Single-crystal X-ray structures were obtained for bis-phenyl (21) and bis-pyrenyl (25) crabs, and for the silver(I) complex (32 and 33) crabs. The silver(I) complex 32 from bis-o-pyridyl crab 30 is a [2+2] dimeric dimetallocyclophane, and 33 from bis-m-pyridyl crab 29 is a [1+1] metallo-bridged cyclophane. The self-assembled intramolecular pi-stacking of pyrenyl rings in 25 with an interplanar distance of 3.40 A and the consequent pi-pi interactions were revealed by the X-ray crystal structure and its luminescence property.

Combination of five- and six-membered rings allows creation of 2,2′:6′,2′′-terpyridine derivatives mimicking the topology of 5,5′-functionalized 2,2′-bipyridine. This molecular design led to the assembly of heterometallic supramolecular networks.

Synthesis of double-threaded ruthenium(ii) ring-in-ring complexes and the Borromean link with three unequal rings detected by mass spectrometry.

A range of oligoaryls that contain alternating benzene-furan rings is synthesized by a rapid convergent/divergent method from the annulation of a propargylic dithioacetal and an aldehyde with a propargylic dithioacetal moiety as a substituent. These oligomers are fairly soluble in a range of organic solvents and can be easily purified by reprecipitation. The substituents on the furan rings can be varied according to the substituents in the starting propargylic dithioacetals. This route provides a useful procedure for the synthesis of alternating benzene-furan oligomers without repeated units. These furan-containing oligoaryls are highly fluorescent in the visible region and are electrochemically active. The band gaps of these oligomers appear to be less sensitive towards changes in conjugation length than those of oligofurans.

Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. e results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.