Characteristic absorption band split of symmetrically tetra-octyloxy metal phthalocyanines

Cong, Fangdi; Wei, Zhen; Huang, Zhiqiang; Yu, Fanglin; Liu, Haixue; Cui, Jing; Yu, Helong; Chu, Xinxin; Du, Xing; Xing, Kun; Lai, Jian-Hong

doi:10.1016/j.dyepig.2015.03.034

Cited by 12 publications

(16 citation statements)

References 51 publications

(80 reference statements)

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“…[27], 4-(n-octyloxy)phthalonitrile (1a) [28], 4-(nhexadecyloxy)phthalonitrile (1b) [29], 4-(n-octylthio)phthalonitrile (1c) [30], 4-(nhexadecylthio) phthalonitrile (1d) [31], 4-(4,7,10-trioxaundecane-1-oxyl)phthalonitrile (1e) [32] and 4-(4,7,10-trioxaundecane-1-sulfanyl)phthalonitrile (1f) [33] were synthesized according to procedures described in the literature. CuPcs, 4d [34], 4e [35] and 4f [35] were prepared by using the method described in the literature.…”

Section: -Nitrophthalonitrilementioning

confidence: 99%

Tetrasubstituted copper phthalocyanines: Correlation between liquid crystalline properties, films alignment and sensing properties

Gülmez

Polyakov

Volchek

et al. 2017

Sensors and Actuators B: Chemical

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Copper phthalocyanines (CuPc) containing alkylthio (-S(CH 2) n CH 3 , n=7 and 15), alkyloxy-(-O(CH 2) n CH 3 , n=7 and 15) and polyoxo (-O(CH 2 CH 2 O) 3 CH 3 and-S(CH 2 CH 2 O) 3 CH 3) substituents were synthesized and investigated to reveal the effects of substituents type (alkylthio, alkyloxy and polyoxo) and the type of the connecting heteroatom (oxygen or sulphur) on the mesogenic properties, films alignment and sensing behaviour. The liquid crystalline properties of these phthalocyanines were investigated by differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction techniques. The structure and morphology of spun thin films of copper phthalocyanine derivatives were studied by the UV-Vis and Raman spectroscopies as well atomic force microscopy. The sensing properties of CuPc films were studied by the measurement of conductivity change upon interaction with ammonia in the range 10-50 ppm. All investigated films of CuPc derivatives display thermotropic columnar mesomorphism. It was shown that the films with polyoxo-(-O(CH 2 CH 2 O) 3 CH 3 and-S(CH 2 CH 2 O) 3 CH 3) substituents as well as with alkylthio-S(CH 2) n CH 3 (n=7) substituents, which are liquid crystalline at room temperature, form ordered films with a random planar alignment of columns. Their films exhibit the better sensor performance with the maximal sensor response for the films of CuPc containing (-S(CH 2 CH 2 O) 3 CH 3) substituents.

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Section: -Nitrophthalonitrilementioning

confidence: 99%

Tetrasubstituted copper phthalocyanines: Correlation between liquid crystalline properties, films alignment and sensing properties

Gülmez

Polyakov

Volchek

et al. 2017

Sensors and Actuators B: Chemical

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“…[15][16][17][18] Among metal phthalocyanines proposed for PDT, those containing Zn remain the most used due to their richly populated triplet excited states and efficient photodynamic production of singlet oxygen and ROS. [15][16][17][18] Among metal phthalocyanines proposed for PDT, those containing Zn remain the most used due to their richly populated triplet excited states and efficient photodynamic production of singlet oxygen and ROS.…”

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confidence: 99%

The heavy atom effect on Zn(ii) phthalocyanine derivatives: a theoretical exploration of the photophysical properties

Alberto

Simone

Mazzone

et al. 2015

Phys. Chem. Chem. Phys.

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Absorption electronic spectra, singlet-triplet energy gaps and spin-orbit matrix elements have been computed at DFT and TDDFT levels of theory for a series of substituted Zn(ii)-phthalocyanines (ZnPcs), recently proposed as potential photosensitizers in photodynamic therapy (PDT). Their photophysical properties have been rationalized in the light of the substitution pattern which includes the position, the donor or withdrawing nature, and the relative donating force of peripheral and non-peripheral ligands. Moreover, the effects of heavy substituents on these properties have been investigated by introducing a different number of iodine atoms on the phthalocyanine macrocycle. The results show that the substitution pattern significantly affects the absorption spectra, but just slightly modifies the ΔES-T values. The presence of heavy atoms produces a significant effect on the photophysical properties of the investigated compounds enhancing the spin-orbit coupling (SOC) values.

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“…Firstly, substrate 1 is activated to intermediate 1a under the coordinated action of alcohol and amine, similar to the effect of serine and histidine in the active site of proteases, 29,30 then intermediate 1a self-polymerizes to polymers, for instance tetramer 1b, which can be further cyclized to 1c. Although intermediate 1c has an inner ring C-N conjugation structure, it is unstable because the conjugation system contains 16- electrons rather than 18- electrons; 25 and therefore 1c is not termed a Pc compound. By inference, after two nitrogen atoms in the C-N conjugation Scheme 2 Proposed mechanism for formation of -NPc from 1; other possible substituent positional isomers of -NPc are omitted for clarity.…”

Section: Paper Synthesismentioning

confidence: 99%

“…701 nm for -BPc (Figure 2), which are typical characteristics of metal-free Pc derivatives with D 2 symmetry. 25 In contrast, -NPc and -NPc, with nitro groups, have low solubility in common organic solvents and are only slightly soluble in DMSO or DMF, which often leads to the aggregation of Pc compounds in solutions. 25,34,35 Especially for -NPc, MS shows that dimer and trimer analogues are present in DMSO in addition to the monomer (S1).…”

Section: Paper Synthesismentioning

confidence: 99%

“…The substance could be slightly dissolved in DMSO and the UV/Vis spectrum of the solution showed that the materiel had an absorption around 700 nm, which is a characteristic Q band absorption of Pc compounds. 25 We thus reasoned that there may be some Pc compound present in the reaction system. Although the yield was very low, the formation of the Pc compound was considered worthy of further attention considering that it was formed at room temperature.…”

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confidence: 99%

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Facile, Mild-Temperature Synthesis of Metal-Free Phthalocyanines

Cong

Jiang

et al. 2021

Synthesis

Self Cite

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It is important for the synthesis and research of phthalocyanine compounds for these compounds to be easily obtained at low temperature. We observed that metal-free phthalocyanine was sometimes found in a simple system used to synthesize phthalocyanine precursors at room temperature, and further studies showed that the key to the effective formation of phthalocyanines at low temperature lay in the presence of equal volumes of alcohol and amine, in addition to substrate phthalonitriles and solvents, in the reaction system. A synthetic mechanism was proposed and facile syntheses have been realized, such as the synthesis of tetra-α(β)-nitrophthalocyanines and tetra-α(β)-(4-tert-butylphenoxy)phthalocyanines from the corresponding substituted phthalonitriles at mild temperature (37 °C). The results are significant for the design and synthesis of new phthalocyanine derivatives, and the method is convenient and easy to adopt for general use in standard laboratories.

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Characteristic absorption band split of symmetrically tetra-octyloxy metal phthalocyanines

Cited by 12 publications

References 51 publications

Tetrasubstituted copper phthalocyanines: Correlation between liquid crystalline properties, films alignment and sensing properties

Tetrasubstituted copper phthalocyanines: Correlation between liquid crystalline properties, films alignment and sensing properties

The heavy atom effect on Zn(ii) phthalocyanine derivatives: a theoretical exploration of the photophysical properties

Facile, Mild-Temperature Synthesis of Metal-Free Phthalocyanines

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