Synthesis of new chromogenic 2,2′-bithiazoylcalix[4]arenes

Oueslati, Farhana; Dumazet‐Bonnamour, Isabelle; Lamartine, R.

doi:10.1016/s0040-4039(01)01755-5

Cited by 26 publications

(11 citation statements)

References 21 publications

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“…A new family of calix[4]arene was prepared by the incorporation of 2,2′-bithiazole units [51]. Water soluble calix[4]arene incorporating both sulfonate groups at its upper rim and 2,2′-bipyridine groups at its lower rim was also prepared [52].…”

Section: Structural Modificationsmentioning

confidence: 99%

Lower-Rim Substituted Calixarenes and Their Applications

Jose

Menon

2007

Bioinorganic Chemistry and Applications

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This review discusses in detail “calixarenes” since their discovery as by-products of the phenol formaldehyde bakelites till the present scenario wherein calixarene has assumed a new dimension in the field of supramolecular chemistry. Extensive literature exists for calixarenes; but herein we have tried to concentrate on the different lower-rim modified calixarenes with their potential applications. An attempt has also been made to critically evaluate the synthesis procedures for different lower-rim substituted calixarenes.

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Section: Structural Modificationsmentioning

confidence: 99%

Lower-Rim Substituted Calixarenes and Their Applications

Jose

Menon

2007

Bioinorganic Chemistry and Applications

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“…In the course of the studies of synthesis of new chromogenic azocalix [4]arene derivatives containing the bithiazole group at lower rim [22], we have extended our research into transition metal cations.…”

Section: Introductionmentioning

confidence: 99%

Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes

Taban

Deligöz

2008

Journal of Hazardous Materials

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“…Because partially lower rim-substituted calixarenes are key intermediates for the design of heterotopic ligands acting as switchable or dual-mode sensors, the development of a convenient method for their synthesis is highly desirable. Unfortunately, there are few literature examples of partially O-alkylated tetranitrocalix[4]arenes (type III) [ 20 , 21 , 22 , 23 ]. They have shown mixed conformational behavior as compared with donor-substituted calixarenes on the upper rim as exemplified by the unusual 1,3-alternate conformation of diallyloxy nitrothiacalix[4]arene in solid state [ 20 ] and a partial cone conformation of mono(ethoxycarbonyl)methoxy calix[4]arene in solution [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Thermally Stable Nitrothiacalixarene Chromophores: Conformational Study and Aggregation Behavior

Muravev

Gerasimova

Fayzullin

et al. 2020

IJMS

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Achieving high thermal stability and control of supramolecular organization of functional dyes in sensors and nonlinear optics remains a demanding task. This study was aimed at the evaluation of thermal behavior and Langmuir monolayer characteristics of topologically varied nitrothiacalixarene multichromophores and phenol monomers. A nitration/azo coupling alkylation synthetic route towards partially O-substituted nitrothiacalixarenes and 4-nitrophenylazo-thiacalixarenes was proposed and realized. Nuclear magnetic resonance (NMR) spectroscopy and X-ray diffractometry of disubstituted nitrothiacalix[4]arene revealed a rare 1,2-alternate conformation. A synchronous thermal analysis indicated higher decomposition temperatures of nitrothiacalixarene macrocycles as compared with monomers. Through surface pressure/potential-molecular area measurements, nitrothiacalixarenes were shown to form Langmuir monolayers at the air–water interface and, through atomic force microscopy (AFM) technique, Langmuir–Blodgett (LB) films on solid substrates. Reflection-absorption spectroscopy of monolayers and electronic absorption spectroscopy of LB films of nitrothiacalixarenes recorded a red-shifted band (290 nm) with a transition from chloroform, indicative of solvatochromism. Additionally, shoulder band at 360 nm was attributed to aggregation and supported by gas-phase density functional theory (DFT) calculations and dynamic light scattering (DLS) analysis in chloroform–methanol solvent in the case of monoalkylated calixarene 3. Excellent thermal stability and monolayer formation of nitrothiacalixarenes suggest their potential as functional dyes.

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Synthesis of new chromogenic 2,2′-bithiazoylcalix[4]arenes

Cited by 26 publications

References 21 publications

Lower-Rim Substituted Calixarenes and Their Applications

Lower-Rim Substituted Calixarenes and Their Applications

Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes

Thermally Stable Nitrothiacalixarene Chromophores: Conformational Study and Aggregation Behavior

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