Near-infrared fluorescence of silicon phthalocyanine carboxylate esters

Amlan K. Pal; Shinto Varghese; David B. Cordes; Alexandra M. Z. Slawin; Ifor D. W. Samuel; Eli Zysman-Colman

doi:10.1038/s41598-017-12374-8

Near-infrared fluorescence of silicon phthalocyanine carboxylate esters

Amlan K. Pal, Shinto Varghese, David B. Cordes, Alexandra M. Z. Slawin, Ifor D. W. Samuel, Eli Zysman-Colman

Research output: Contribution to journal › Article › peer-review

Abstract

Seven silicon(IV) phthalocyanine carboxylate esters (SiPcs, 1–7) with non-, partially- and per-fluorinated aliphatic (linear or branched at the alpha-carbon) and aromatic ester groups have been synthesized, their solid-state structures determined and their optoelectronic properties characterized. The SiPcs exhibit quasi-reversible oxidation waves (vs. Fc⁺/Fc) at 0.58–0.75 V and reduction waves at −0.97 to −1.16 V centered on the phthalocyanine ring with a narrow redox gap range of 1.70–1.75 V. Strong absorbance in the near-infrared (NIR) region is observed for 1–7 with the lowest-energy absorption maximum (Q band) varying little as a function of ester between 682 and 691 nm. SiPcs 1–7 fluorescence in the near-infrared with emission maxima at 691–700 nm. The photoluminescence quantum yields range from 40 to 52%. As a function of esterification, the SiPcs 1–7 exhibit moderate-to-good solubility in chlorinated solvents, such as 1,2-dichlorobenzene and chloroform.

Original language	English
Article number	12282
Number of pages	14
Journal	Scientific Reports
Volume	7
DOIs	https://doi.org/10.1038/s41598-017-12374-8
Publication status	Published - 25 Sept 2017

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Cite this

@article{f75793335bfa4c75928568688ff132d5,

title = "Near-infrared fluorescence of silicon phthalocyanine carboxylate esters",

abstract = "Seven silicon(IV) phthalocyanine carboxylate esters (SiPcs, 1–7) with non-, partially- and per-fluorinated aliphatic (linear or branched at the alpha-carbon) and aromatic ester groups have been synthesized, their solid-state structures determined and their optoelectronic properties characterized. The SiPcs exhibit quasi-reversible oxidation waves (vs. Fc+/Fc) at 0.58–0.75 V and reduction waves at −0.97 to −1.16 V centered on the phthalocyanine ring with a narrow redox gap range of 1.70–1.75 V. Strong absorbance in the near-infrared (NIR) region is observed for 1–7 with the lowest-energy absorption maximum (Q band) varying little as a function of ester between 682 and 691 nm. SiPcs 1–7 fluorescence in the near-infrared with emission maxima at 691–700 nm. The photoluminescence quantum yields range from 40 to 52%. As a function of esterification, the SiPcs 1–7 exhibit moderate-to-good solubility in chlorinated solvents, such as 1,2-dichlorobenzene and chloroform.",

author = "Pal, {Amlan K.} and Shinto Varghese and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Samuel, {Ifor D. W.} and Eli Zysman-Colman",

note = "EZ-C acknowledges the University of St Andrews for financial support. We are grateful to the EPSRC for financial support from grant EP/M02105X/1 and the European Research Council for financial support from grant 321305. I.D.W.S. acknowledges a Royal Society Wolfson Research Merit Award.",

year = "2017",

month = sep,

day = "25",

doi = "10.1038/s41598-017-12374-8",

language = "English",

volume = "7",

journal = "Scientific Reports",

issn = "2045-2322",

publisher = "Nature publishing group",

}

TY - JOUR

T1 - Near-infrared fluorescence of silicon phthalocyanine carboxylate esters

AU - Pal, Amlan K.

AU - Varghese, Shinto

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Samuel, Ifor D. W.

AU - Zysman-Colman, Eli

N1 - EZ-C acknowledges the University of St Andrews for financial support. We are grateful to the EPSRC for financial support from grant EP/M02105X/1 and the European Research Council for financial support from grant 321305. I.D.W.S. acknowledges a Royal Society Wolfson Research Merit Award.

PY - 2017/9/25

Y1 - 2017/9/25

N2 - Seven silicon(IV) phthalocyanine carboxylate esters (SiPcs, 1–7) with non-, partially- and per-fluorinated aliphatic (linear or branched at the alpha-carbon) and aromatic ester groups have been synthesized, their solid-state structures determined and their optoelectronic properties characterized. The SiPcs exhibit quasi-reversible oxidation waves (vs. Fc+/Fc) at 0.58–0.75 V and reduction waves at −0.97 to −1.16 V centered on the phthalocyanine ring with a narrow redox gap range of 1.70–1.75 V. Strong absorbance in the near-infrared (NIR) region is observed for 1–7 with the lowest-energy absorption maximum (Q band) varying little as a function of ester between 682 and 691 nm. SiPcs 1–7 fluorescence in the near-infrared with emission maxima at 691–700 nm. The photoluminescence quantum yields range from 40 to 52%. As a function of esterification, the SiPcs 1–7 exhibit moderate-to-good solubility in chlorinated solvents, such as 1,2-dichlorobenzene and chloroform.

AB - Seven silicon(IV) phthalocyanine carboxylate esters (SiPcs, 1–7) with non-, partially- and per-fluorinated aliphatic (linear or branched at the alpha-carbon) and aromatic ester groups have been synthesized, their solid-state structures determined and their optoelectronic properties characterized. The SiPcs exhibit quasi-reversible oxidation waves (vs. Fc+/Fc) at 0.58–0.75 V and reduction waves at −0.97 to −1.16 V centered on the phthalocyanine ring with a narrow redox gap range of 1.70–1.75 V. Strong absorbance in the near-infrared (NIR) region is observed for 1–7 with the lowest-energy absorption maximum (Q band) varying little as a function of ester between 682 and 691 nm. SiPcs 1–7 fluorescence in the near-infrared with emission maxima at 691–700 nm. The photoluminescence quantum yields range from 40 to 52%. As a function of esterification, the SiPcs 1–7 exhibit moderate-to-good solubility in chlorinated solvents, such as 1,2-dichlorobenzene and chloroform.

UR - https://www.nature.com/articles/s41598-017-12374-8#Sec13

U2 - 10.1038/s41598-017-12374-8

DO - 10.1038/s41598-017-12374-8

M3 - Article

SN - 2045-2322

VL - 7

JO - Scientific Reports

JF - Scientific Reports

M1 - 12282

ER -

Near-infrared fluorescence of silicon phthalocyanine carboxylate esters

Abstract

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