Template 1,8-naphthalenedicarboxylic acid

Zinc naphthalocyanine has been prepared in low yield (18%) by the template reaction of Zn(02CMe)2, urea and 2,3-naphthalenedicarboxylic acid.1138 The synthesis of zinc tetra-2,3-naphthoporphine by a template reaction has been described.1139... 

The ability of a SCSC reaction to occur within a finite molecular assembly based on a linear template was first demonstrated by MacGillivray and co-workers who utilized 1,8-naphthalenedicarboxylic acid as a template to assemble trans-1-(3-pyridyl)-2-(4-pyridyl)ethylene, via O-H - -N hydrogen bonds, fora regioconotrlled [2+2] photodimerization [55]. The SCSC reaction was found to proceed, upon UV-irradiation with 420 nm light, quantitatively to give the head-to-head photoproduct rctt-l,2-bis(3-pyridyl)-3,4-bis(4-pyridyl)cyclobutane. A comparison of the single-... 

MacGillivray and coworkers also described a dicar-boxylic acid that acted as a template (Figure 3). ° Cocrystallization of 1,8-naphthalenedicarboxylic acid (1,8-nda) with either 4,4 -bpe or 2,2 -bpe produced four-component assemblies sustained by four 0-H- N hydrogen bonds (Figure 3a). The olefins were parallel and separated by a distance of 3.73 and 3.91 A, respectively, which rendered 4,4 -bpe and 2,2 -bpe photoactive. UV irradiation of each solid produced the corresponding rcff-cyclobutanes in quantitative yield. In a related work, Jones demonstrated the ability of a triacid to act as a template. Specifically, cocrys-fallization of tricarballylic acid (tea) with 4,4 -bpe afforded... 

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