Surface plasmon resonance of self-assembled phthalocyanine monolayers: possibilities for optical gas sensing

Simpson, Tim R. E.; Cook, Michael J.; Petty, Michael C.; Thorpe, S.C.; Russell, David A.

doi:10.1039/an9962101501

Cited by 42 publications

(19 citation statements)

References 8 publications

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“…Compounds of series 3 also form LB films but also act as precursors to series 4 [24]. The latter form selfassembled monolayer (SAM) films on gold slides [25,26]. Reflection-absorption infrared spectroscopy (RAIRS) indicates that the angle between the plane of the ring and the substrate surface increases as the length of the tethering chain is increased from (CH 2 ) 3 through (CH 2 ) 8 to (CH 2 ) 11 [27].…”

Section: :1 Phthalocyaninesmentioning

confidence: 99%

Non-uniformly substituted phthalocyanines and related compounds: alkylated tribenzo-imidazolo[4,5]- porphyrazines

Bakboord

Cook

Hamuryudan

2000

J. Porphyrins Phthalocyanines

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The synthesis and properties of ‘3:1’ phthalocyanines, in which three of the benzenoid rings are similarly substituted whereas the fourth is differently substituted or is replaced by a heteroaromatic ring, are overviewed with an emphasis on contributions from the group at the University of East Anglia. The synthesis of novel hepta-alkylated tribenzo-imidazolo[4,5]porphyrazines as metal-free derivatives by cross-condensation of 3,6-dialkylphthalonitrile and 1-alkyl-4,5-dicyanoimidazole is described. The compounds show Q band absorption at 701 and 660 nm. The Q band is thus hypsochromically shifted relative to the Q band absorption of the corresponding metal-free octa-alkylphthalocyanines and the metal-free hexa-alkylated derivatives of tribenzo-pyridino[3,4]porphyrazines, tribenzo-thiopheno[2,3]porphyrazines and tribenzo-thiopheno[3,4]porphyrazines. Examples of the tribenzo-imidazolo[4,5]porphyrazines have been deposited as smooth, even and transparent spin-coated films with broad-band absorption in the region 600-750 nm.

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Section: :1 Phthalocyaninesmentioning

confidence: 99%

Non-uniformly substituted phthalocyanines and related compounds: alkylated tribenzo-imidazolo[4,5]- porphyrazines

Bakboord

Cook

Hamuryudan

2000

J. Porphyrins Phthalocyanines

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“…The changes in optical and electrical properties of porphyrin and phthalocyanine assemblies during interactions with other small molecules have been the basis of chemical sensor transducer layers for some time [29][30][31][32]. The high molar absorptivities in the visible for these molecules, coupled with the tendency for rather large changes in these absorption spectra during oxidation and reduction, have suggested to investigators that these changes could be exploited in sensors where small absorbance changes are easily detected (e.g.…”

Section: New Optical Properties From Isolated Phthalocyanines and Pormentioning

confidence: 99%

Phthalocyanines and porphyrins as materials

Armstrong

2000

J. Porphyrins Phthalocyanines

115

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Several recent studies of phthalocyanines and porphyrins as materials in emerging technologies are reviewed here. Emphasis is placed on the use of these materials as components in building materials where the symmetry, optical and electrical properties of the molecule are important. Aggregates or polymers of these molecules have been known for some time to possess interesting electrical conductivities, and more recently interesting optical properties. Their optical properties as isolated species in condensed phases have also recently become interesting, and their ability to form new hybrid materials, by mixing or by thin film deposition, with other molecules with different electron affinities and ionization potentials, now appears to be extremely attractive. Device technologies in which we can anticipate these molecules appearing in the near future include organic light-emitting diodes, organic field effect transisitors, organic photovoltaics, optical limiters and optically based chemical sensors.

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“…These compounds are capable of coordinating many elements of the Periodic Table, including lanthanides, to form coordination compounds with various structures, both single-decker and sandwich-like [4]. The latter may be used as sensors [5][6][7], materials for ionizing radiation detectors [8], dyes for passive synchronization of laser modes [9], and electrochromic materials [10]. Among numerous sandwich-like complexes, mixed-ligand coordination compounds containing tetrabenzoporphyrin and phthalocyanine fragments were studied most poorly [11,12], whereas coordination compounds based on tetrabenzocorrins were not reported at all.…”

mentioning

confidence: 99%

Synthesis and spectral parameters of symmetric and unsymmetrical sandwich-like double- and triple-decker lanthanide complexes containing 1-methyltetrabenzooctadehydrocorrin and phthalocyanine fragments

2011

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Single-and double-decker lanthanide complexes with 1-methyltetrabenzooctadehydrocorrin were synthesized by reaction of 3-[(1-hydroxy-1-methyl-1H-isoindol-3-yl)methylidene]-2,3-dihydro-1H-isoindol-1-one with hydrazine hydrate in the presence of lanthanide acetates. Heating of the former with phthalonitrile gave unsymmetrical double-and triple-decker complexes containing 1-methyltetrabenzooctadehydrocorrin and phthalocyanine fragments. Spectral properties of the synthesized complexes were studied.Phthalocyanines and porphyrins constitute two most important classes of tetrapyrrole pigments [1-3]. These compounds are capable of coordinating many elements of the Periodic Table, including lanthanides, to form coordination compounds with various structures, both single-decker and sandwich-like [4]. The latter may be used as sensors [5][6][7], materials for ionizing radiation detectors [8], dyes for passive synchronization of laser modes [9], and electrochromic materials [10]. Among numerous sandwich-like complexes, mixed-ligand coordination compounds containing tetrabenzoporphyrin and phthalocyanine fragments were studied most poorly [11,12], whereas coordination compounds based on tetrabenzocorrins were not reported at all.The present work was aimed at synthesizing homoand heteroligand lanthanide complexes containing 1-methyltetrabenzooctadehydrocorrin and phthalocyanine fragments and studying their spectral properties. As reported previously [13], single-decker 1-methyltetrabenzooctadehydrocorrin complex I with hydroxylanthanum can be prepared by reaction of 3-[(1-hydroxy-1-methyl-1H-isoindol-3-yl)methylidene]-2,3-dihydro-1H-isoindol-1-one (II) with hydrazine hydrate in the presence of lanthanum(III) acetate in boiling butan-1-ol (reaction time 3 h). We applied a similar procedure to obtain analogous lutetium and erbium complexes III and IV. In addition, we found that the reaction performed with a deficiency of metal salt gives mainly double-decker bis(1-methyltetrabenzooctadehydrocorrin) complexes of lutetium, erbium, and lanthanum (compounds V-VII). Thus the synthesis of single-and double-decker lanthanide complexes with 1-methyltetrabenzooctadehydrocorrin may be illustrated by Scheme 1.When the reaction was complete, in each case the mixture was diluted with toluene. Most unreacted compound II and metal salt separated from the solution, while corrin metal complexes remained dissolved. The precipitate was filtered off, and the filtrate was subjected to column chromatography on aluminum oxide using toluene as eluent, the first bright green fraction being collected. We thus succeeded in separating the target metal complexes from by-products. Unlike initial compound II and products of its reaction with hydrazine (brown tarry substances), corrin metal complexes are readily soluble in toluene-butan-1-ol and are characterized by high chromatographic mobility on aluminum oxide (R f 0.70-0.85).Compounds I and III-VII were isolated as dark green crystalline substances that are readily soluble in toluene, acetone, DMF, and ch...

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Surface plasmon resonance of self-assembled phthalocyanine monolayers: possibilities for optical gas sensing

Cited by 42 publications

References 8 publications

Non-uniformly substituted phthalocyanines and related compounds: alkylated tribenzo-imidazolo[4,5]- porphyrazines

Non-uniformly substituted phthalocyanines and related compounds: alkylated tribenzo-imidazolo[4,5]- porphyrazines

Phthalocyanines and porphyrins as materials

Synthesis and spectral parameters of symmetric and unsymmetrical sandwich-like double- and triple-decker lanthanide complexes containing 1-methyltetrabenzooctadehydrocorrin and phthalocyanine fragments

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