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One‐Pot Synthesis of Highly Emissive Dipyridinium Dihydrohelicenes
Author(s) -
Santoro Amedeo,
Lord Rianne M.,
Loughrey Jonathan J.,
McGowan Patrick C.,
Halcrow Malcolm A.,
Henwood Adam F.,
Thomson Connor,
ZysmanColman Eli
Publication year - 2015
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.201406255
Subject(s) - hydrobromide , chemistry , dihedral angle , amine gas treating , condensation , derivative (finance) , cytotoxicity , crystal (programming language) , stereochemistry , crystallography , medicinal chemistry , organic chemistry , molecule , physics , in vitro , hydrogen bond , biochemistry , computer science , financial economics , economics , thermodynamics , programming language
Condensation of a pyridyl‐2‐carbaldehyde derivative with 2‐(bromoethyl)amine hydrobromide gave tetracyclic pyrido[1,2‐ a ]pyrido[1′,2′:3,4]imidazo‐[2,1‐ c ]‐6,7‐dihydropyrazinium dications in excellent yields. Crystal structures and NOE data demonstrated the helical character of the dications, the dihedral angles between the two pyrido groups ranging from 28–45°. An intermediate in the synthesis was also characterized. A much brighter emission compared to literature helicenes has been found, with quantum yields as high as 60 % in the range of λ =460–600 nm. Preliminary cytotoxicity studies against HT‐29 cancer cells demonstrated moderate‐to‐good activity, with IC 50 values 12–30× that of cisplatin.