Tris(ferrocenylmethidene)sumanene: synthesis, photophysical properties and applications for efficient caesium cation recognition in water

Abstract

<p>Tris(ferrocenylmethidene)sumanene was synthesized, characterized and applied for caesium cation recognition in water.</p>

Disaggregation of a sumanene-containing fluorescent probe towards highly sensitive and specific detection of caesium cations

“…† The formation of a pure compound was confirmed using NMR spectroscopy, high-resolution mass spectrometry (HRMS) and elemental analysis (see the ESI, † for the compound characterization data). Similar to other sumanene derivatives prepared using the method described herein, 16,23 the NMR analyses revealed the formation of diastereoisomers (unsymmetrical and C 3 symmetric).…”

“…This revealed that the 5: Cs + complex stoichiometry was 1 : 2. Due to our previous studies on the interactions between Cs + and sumanene derivatives in their neutral state, 15,16 this finding suggests that the driving force of the observed disaggregation behaviour was indeed the formation of the sandwich complex between Cs + and two sumanene molecules. To confirm this further, cold spray ESI-MS analysis was performed with a mixture comprising compound 5 and 25 equiv.…”

“…Recently, we reported that sumanene is also able to interact with Cs + in its neutral state. 15,16 This interaction is driven by the site-selective cation-p-interaction that occurs following inclusion in the concave site of sumanene. [17][18][19] We have demonstrated that the Cs + recognition process is specific and effective for the ferrocene-functionalized sumanenes.…”

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

“…In another study, the same group has also reported a series of both C 3 -symmetric as well as unsymmetric diastereomeric π-conjugated bowl-shaped molecules 37a–f in good to quantitative yields ( Scheme 6 ) [ 34 – 35 ]. These π-conjugated systems were assembled by treating sumanene ( 2 ) with different conjugated aromatic aldehydes using 30% aqueous NaOH in the presence of TBAB in THF.…”

The core of the matter – arene substitution determines the coordination and catalytic behaviour of tris(1-phosphanyl-1′-ferrocenylene)arene gold(i) complexes

“…Notable examples include the BIFEP (II) and TRAP (III) ligand families, 16,17 mesoionic carbene IV, 18 terferrocene-based bis(terpyridine) V, 19 and C 2 -symmetric tetradentate TriFer VI. 20 Furthermore, a number of discrete multiferrocenyl compounds [21][22][23][24][25][26][27] and ferrocenyl-containing dendrimers have been reported over the last years. [28][29][30][31] Conceived as small-molecule analogues of redox-switchable dendrimers, [32][33][34] we have recently reported the synthesis of a new family of tris-phosphanes 1 (Chart 1) incorporating a redox-active, C 3 -symmetric tris(ferrocenyl)arene backbone.…”