Towards A,D‐(1,10‐Phenanthroline)‐Bridged Calix[6]arene Dendrimers | Zendy

Eggert Jan P. W. | Zendy; Lüning Ulrich | Zendy

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Towards A,D‐(1,10‐Phenanthroline)‐Bridged Calix[6]arene Dendrimers

Author(s) -

Eggert Jan P. W.,

Lüning Ulrich

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200700639

Subject(s) - sonogashira coupling , chemistry , dendrimer , phenanthroline , trimethylsilyl , yield (engineering) , dimer , stereochemistry , medicinal chemistry , polymer chemistry , crystallography , organic chemistry , catalysis , palladium , materials science , metallurgy

5‐Bromo‐2,9‐bis(bromomethyl)‐1,10‐phenanthroline ( 5 ) has been synthesized starting from 5‐bromo‐2,9‐dimethyl‐1,10‐phenanthroline ( 1 ) in overall yields of up to 53 % by two approaches. Next, calix[6]arene ( 7 ) was bridged with 5 , giving the A,D‐bridged bimacrocyle 9 in 42 % yield. Under application of Sonogashira reaction conditions, trimethylsilyl‐protected ethyne was first coupled to the 5‐position of the 1,10‐phenanthroline, and the ethyne unit was then deprotected and connected with 1,3,5‐triiodobenzene ( 12 ) as a trivalent core. A trimeric first‐generation dendrimer 13 was formed, together with a Glaser dimer sideproduct, and could be isolated in 36 % yield. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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