Abstract
New pyridine-functionalised pyrazole compounds [HpzR(n)py] (R(n) = C6H4OCnH2n+1; n = 12, 14, 16, 18; 1-4) and their corresponding silver complexes [Ag(HpzR(n)py) 2][A] ([A] = NO3-, BF4-; 5-12) have been synthesised and characterised. All of them, with the exception of 1, are liquid crystal materials exhibiting monotropic or enantiotropic SmA mesophases, in contrast to the non-mesomorphic related R(n)-monosubstituted compounds. Because the molecular shape is a factor determinant in the organisation of molecules in the liquid crystal phase, we were interested in solving the crystal structure of representative examples of the mentioned compounds, such as 1 and 6. So, the X-ray crystal structure of [Hpz R(12)py] 1 shows the presence of dimeric units through N-H⋯N hydrogen bonds, which conform to an elongated molecular shape containing a double chain length. On the other hand, the structure of [Ag(Hpz R(14)py)2][NO3] 6 also evidenced Ag-Ag bonded dimers from 'U'-shaped cationic entities. These dimers exhibit four chains, two by two alternated, so giving rise to a longer molecular length. Of particular interest was to observe that in both structures, the dimers are layer-like packed, their lamellar structures being related to that of the mesophases found in both kinds of compounds. Furthermore, the analysis of the optical data of the compounds 2 and 4 and the silver compounds 5, 6, 9 and 10 as representative examples pointed out their luminescent behaviour as well as their good ability to act as fluorescent probes for Zn2+, Cu2+ and Ag +. An increase in the fluorescence quantum yields is observed in the final complexes produced in the titrations, this fact being specially notable when 9 was used as the starting compound. © The Royal Society of Chemistry 2013.
Original language | English |
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Pages (from-to) | 2107-2120 |
Number of pages | 14 |
Journal | Dalton Transactions |
Volume | 42 |
Issue number | 6 |
DOIs | |
Publication status | Published - 14 Feb 2013 |
Keywords
- Dimers
- Hybrid materials
- Hydrogen bonds
- Liquid crystals
- Quantum yield
- Silver compounds
- Dimeric units
- Double chain
- Fluorescence quantum yield
- Fluorescent probes
- Liquid crystal materials
- Liquid crystal phase
- Mesophases
- Molecular length
- Molecular shapes
- Multi-functional materials
- Non-mesomorphic
- Optical data
- Pyrazoles
- Silver complexes
- Starting compounds
- X ray crystal structures
- Silver