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The Self‐Assembly of a Lipophilic Deoxyguanosine Derivative and the Formation of a Liquid‐Crystalline Phase in Hydrocarbon Solvents
Author(s) -
Gottarelli Giovanni,
Masiero Stefano,
Mezzina Elisabetta,
Spada Gian Piero,
Mariani Paolo,
Recanatini Maurizio
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19981111)81:11<2078::aid-hlca2078>3.0.co;2-7
Subject(s) - chemistry , deoxyguanosine , lyotropic , ribbon , crystallography , liquid crystal , phase (matter) , lyotropic liquid crystal , liquid crystalline , hydrocarbon , derivative (finance) , organic chemistry , stereochemistry , adduct , physics , geometry , mathematics , optics , financial economics , economics
The lipophilic 3′,5′‐di‐ O ‐decanoyl‐2′‐deoxyguanosine ( 1 ) in CHCl 3 undergoes extensive self‐assembly, mediated by H‐bonding between the guanine bases, to give ribbon‐like aggregates. X‐Ray investigation of the platelets obtained from CHCl 3 reveals a disordered fibre‐like structure consisting of stacks of the ribbon‐like aggregates. The aggregates are completely different from the columnar structures, based on G‐quartets, which are the building blocks of the mesophases formed by deoxyguanosine oligonucleotides in H 2 O. In pure hydrocarbons or in CHCl 3 /hydrocarbons, 1 forms a lyotropic liquid‐crystalline phase.