Linear Heterocyclic Aromatic Fluorescence Compounds Having Various Donor–Acceptor Spacers Prepared by the Combination of Carbon–Carbon Bond and Carbon–Nitrogen Bond Cross-Coupling Reactions

Abstract

A family of novel linear 1,10-phenanthroline-based (A-D-A-D-A) and oligothiophene-based (A-D-D-D-(D)-A) heterocyclic aromatic fluorescence compounds having N-containing imidazole and pyridine tails with effective π-conjugated systems, prepared by the combination of carbon-carbon (C-C) bond and carbon-nitrogen (C-N) bond cross-coupling reactions, is described. They have molecular lengths of more than 2.30 nm in the cases of 4, 6, 9, and 26, various D-A spacers, and certain N-coordination sites (phen, imidazole, and pyridine). X-ray single-crystal structures of 13 compounds reveal a variety of trans and cis configurations with different dihedral angles between adjacent aromatic heterocycles. Synthetic, computational, and spectral studies have been made to reveal the differences between cross-coupling approaches on the C-C bond and C-N bond formation as well as band gaps and energy levels and optical and electrochemical properties for related compounds. The influences of introducing a β-methyl group to the thiophene ring on reaction activity, solubility, and conformation of related compounds have also been discussed.

Cell‐Compatible Fluorescent Chemosensor for Zn2+ Based on a 3,8‐Extended 1,10‐Phenanthroline Derivative

“…Comparative experiments on Zn 2+ ‐sensing characteristics were carried out with 10 μ M Phen, PHT0,6c PHT1, and PHT211b solutions with the addition of 1 equiv. Zn 2+ .…”

C–C bond cleavage in acetonitrile by copper(ii)–bipyridine complexes and in situ formation of cyano-bridged mixed-valent copper complexes

“…Dbphen, mkphen and dkphen were synthesized by the methods reported in literature, [58][59][60] and the preparation of dtphen and dbtphen compounds has been previously reported by our lab. [61][62][63] As shown in Table 5, dmbpy exhibits similar reactivity to bpy, while dbphen has no activity at all because of the large steric hindrance effects of two n-butyl groups at positions 2 and 9 of phen. Attributed to the oxidability of mkphen and dkphen, the required reaction does not proceed.…”

Coplanar Bithiazole-Centered Heterocyclic Aromatic Fluorescent Compounds Having Different Donor/Acceptor Terminal Groups

“…In our previous work, a series of 1,10-phenanthroline-based and oligothiophene-based heterocyclic aromatic compounds with terminal thienyl, imidazolyl, and pyridyl groups has been described . Furthermore, temperature-dependent semiconducting and photoresponsive properties of self-assembled nanocomposite films and nanodevices fabricated from these compounds and their metal complexes have been explored .…”