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Oligospiroketals as Novel Molecular Rods
Author(s) -
Wessig Pablo,
Möllnitz Kristian,
Eiserbeck Christiane
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700108
Subject(s) - pentaerythritol , solubility , cyclohexane , terminal (telecommunication) , rod , chemistry , modular design , combinatorial chemistry , stereochemistry , organic chemistry , computer science , medicine , telecommunications , alternative medicine , fire retardant , pathology , operating system
A modular approach for the synthesis of molecular rods based on oligospiroketals has been developed. The strategy relies on different terminal and intermediate segments, which are joined by ketal formation between ketones and diols. For this purpose it was necessary to develop a new ketalization method to circumvent some problems related with the established methods. The terminal segments are either derived from 4‐piperidinone or from 4‐oxocyclohexane carboxylic acid whereas the intermediate segments rest on pentaerythritol and cyclohexane‐1,4‐dione. A series of trispiro ( 14 – 18 ), hexaspiro ( 19 ) and nonaspiro ( 20 ) compounds have been prepared and characterized. From these we realized that it is imperative to use solubility enhancing groups if more than seven rings are joined.