Practical synthesis of new functionalized tetraphenylenes

The practical synthesis procedure of substituted tetraphenylene derivatives involving the synthesis of a precursor for 4, 7-dunethoxyisobenzofuran and Diets-Alder addition of 4, 7-dimethoxyisobenzofuran generated in situ to 5, 6, 11,12-te-tradehydrodibenzo[a,e]cyclooctene, followed by a low valent titanium mediated deoxygenation to give 1,4, 11, 14-tetra-methoxy-dibenzo[b, n] tetraphenylene, which can be further demethyiated to the corresponding phenolic compound, which was acetylated to afford 1,4,11,14-tetraacetoxy-dibenzo-[ b, n] tetraphenylene.     

Chemistry of 1,16-Dihydroxytetraphenylene and 2,3,9,10-Tetrakis(trimethylsilyl) pentacene

Recently, four tetraphenylenols, as well as several non-substituted and substituted 2,3,9,10-tetrakis(trimethylsilyl)pentacenes were realized in our laboratories. In this presentation, the synthesis, hydrogen bonding properties, and chiral recognition studies of (S)- 1,16-dihydroxytetraphenylene (1) and its (R)-enantiomer will be delineated.1,16-Bis(diphenylphosphino)tetraphenylene (2) was also realized from 1 and was employed in the formation of a stable platinum complex. The synthesis of soluble 2,3,9,10-tetrakis(trimethylsilyl)pentacene (3) was achieved and fully characterized by physical and spectroscopic methods.     

Enantioselective Brønsted base catalyzed [4+2] cycloaddition using novel amino-substituted tetraphenylene derivatives

This paper is concerned with the syntheses of 1,8,9,16-tetrahydroxytetraphenylene derivatives and their applications as Brønsted base organocatalysts for [4+2] cycloaddition between anthrone and maleimides. The structural modifications of the catalysts and their related catalytic properties are described and discussed in details.     

Synthesis of 1,4,5,16-tetrahydroxytetraphenylene

This paper concerns the synthesis of 1,4,5,16-tetrahydroxytetraphenylene, which may function as a building block for the construction of molecular scaffolds. The synthesis of 1,4,5,16-tetrahydroxytetraphenylene was realized by stepwise Diels-Alder reactions to form two benzene rings using 1,10-dimethoxydibenzo[a,e]cyclooctene as a precursor. This key intermediate, in turn, could be obtained by photo-rearrangement of its corresponding barrelene.     

2,3,10,11‐Tetrahydroxytetraphenylene and Its Application in Molecular Recognition

A rationally designed 2,3,10,11‐tetrahydroxytetraphenylene ( 1 ) has been synthesized. Employing 1 as a building block, a structurally novel tweezer‐like host 2 containing dibenzo‐24‐crown‐8 moieties has been prepared. Host 2 showed excellent molecular‐recognition ability toward paraquat (=1,1′‐dimethyl‐4,4′‐bipyridinium dichloride) derivative 3a to form a 1 : 1 stable complex in solution.     

Preparation and crystal structure of a 1:1 inclusion compound of 1,4,11,14-tetramethoxy-dibenzo[b,n]tetraphenylene with pyridine

The new host 1,4,11,14-tetramethoxy-dibenzo[b,n]tetraphenylene forms a 1:1 inclusion compound with pyridine, in which a pair of centrosymmetrically-related guest species are enclosed in the cage surrounded by six host molecules. C₃₆H₂₈O₄·C₅H₅N, F_W=603.68, triclinic, space group P-1, a=11.796(2), b=16.075(3), c=9.004(2) Å; =98.39(3)°, β=90.01(3)°, γ=108.19(3)°, V=1602.8(5) Å³, Z=2, F(000)=636, D_c=1.251 g/cm³, μ=0.080 mm⁻¹. The final R indices [I>2σ(I)] R₁=0.0759, wR₂=0.1970 for 5623 MoK observed data.