Synthesis and Properties of Copper(II) Phthalocyanines with Monoazacrown and Crown Ethers as Peripheral Substituents

Abstract

<jats:p> Soluble and less soluble phthalocyaninatocopper(II) derivatives (4a and 4b) were prepared from the corresponding 7-[(4′-benzo-15-crown-5)oyl]-15, 16-dibromo-2,3,6,7,8,9,11,12-octahydro-5H-benzo[e]-[1,4,10,13,7] tetraoxaazacyclopentadecine (3a) and 7-(2′-tosylaminoethyl)-15, 16-dibromo-2,3,6,7,8,9,11, 12-octahydro-5H-benzo[e]-[1,4,10,13,7] tetraoxaazacyclopentadecine (3b) and CuCN in pyridine. A less soluble novel multifunctionalized scorpiand macrocycle-substituted phthalocyanine (4c) in which an NH <jats:sub>2</jats:sub> CH <jats:sub>2</jats:sub> CH <jats:sub>2</jats:sub>— chain is appended to a monoazacrown ether ring was obtained by detosylation of 4b with concentrated sulfuric acid. </jats:p>

Functional fluoro substituted tetrakis-metallophthalocyanines: Synthesis, spectroscopy, electrochemistry and spectroelectrochemistry

“…), and electron-donating (-NH 2 , Ar-S-, RO-, etc.) bulky or long chain groups [11][12][13][14][15][16]. Metal phthalocyanines bearing fluorine atoms are currently receiving a great deal of attention due to their high thermal and chemical stability; they also possess interesting electron-transporting characteristics [17].…”

Selective heavy metal receptor functional phthalocyanines bearing thiophenes: Synthesis, characterization, spectroscopy and electrochemistry

“…3 (A and B), the titrations show clear isosbestic points at 326, 372, 403, 470, 607, 624, 669 and 710 nm for 2 and 362, 420, 642 and 709 nm for 3. This observation is in harmony with the previously reported studies [15,18,19,29,30].…”

“…Therefore, functional phthalocyanines are of particular chemical interest because of their tendency to aggregate in self-assemblies, optical and electrochemical responses to specific analyte, and capable of binding multiple metal ions for the development of new molecules/macrocycles [14e17]. For example, phthalocyanines bearing thia-oxo functionalities show optical changes when they bind Ag I and Pd II ions [18,19], while crown-attached phthalocyanines are well suited to bind alkaline and alkaline earth metal ions [14,15,20,21].…”

Synthesis of some 3-phenyl chromenone-crown ethers and equilibrium studies on complexation with ion-pair extraction of sodium and potassium dyes

“…(1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) [35]. The equilibrium processes taking place during the extraction between an aqueous solution containing the alkali metal cation, M + (w) , and organic anion, A À (w) , and an organic solution containing crown ethers L (org) , can be written as:…”

“…The particular role of liquidliquid alkali cation transfer in membranes has expanded the area of interest. The cation binding selectivity of such molecules, particularly the crown ethers, have been investigated with different types of macrocyclic structures by several authors and have been well documented for molecular recognition [11][12][13][14]. The determination of sodium by means of ion-selective electrodes involving the use of crown ethers has been reported, as has their use as potentiometric titrants [15][16][17][18].…”