Synthesis and characterisation of some 1,4,8,11,15,18,22,25-octa(alkoxymethyl)phthalocyanines: A new series of discotic liquid crystals

Andrew N. Cammidge; Michael J. Cook; Kenneth J. Harrison; Neil B. McKeown

doi:10.1039/P19910003053

Synthesis and characterisation of some 1,4,8,11,15,18,22,25-octa(alkoxymethyl)phthalocyanines: A new series of discotic liquid crystals

Andrew N. Cammidge, Michael J. Cook, Kenneth J. Harrison, Neil B. McKeown

Synthetic and Medicinal Chemistry

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

70 Citations (Scopus)

Abstract

A series of 3, 6-bis(alkoxymethyl)phthalonitriles, prepared via Diels–Alder reactions of 2, 5-bis(alkoxymethyl)furans with fumaronitrile, have been converted into the corresponding phthalocyanines. Zn(II) and Cu(II) derivatives of 1,4,8,11,15,18,22,25-octa(heptyloxymethyl)phthalocyanine were also prepared. Examples of the macrocycles were characterised using 1H NMR spectrometry and optical spectroscopy. Those bearing straight chains aggregate in solutions of chloroform and toluene. The octa(butoxymethyl)phthalocyanine and its longer chain homologues exhibit a discotic liquid crystallinephase. Compounds containing branched sidechains are liquid crystals at room temperature.

Original language	English
Pages (from-to)	3053-3058
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	12
DOIs	https://doi.org/10.1039/P19910003053
Publication status	Published - 1991

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10.1039/P19910003053

Cite this

@article{86c947dbc49b44ff9fce59258c89c09c,

title = "Synthesis and characterisation of some 1,4,8,11,15,18,22,25-octa(alkoxymethyl)phthalocyanines: A new series of discotic liquid crystals",

abstract = "A series of 3, 6-bis(alkoxymethyl)phthalonitriles, prepared via Diels–Alder reactions of 2, 5-bis(alkoxymethyl)furans with fumaronitrile, have been converted into the corresponding phthalocyanines. Zn(II) and Cu(II) derivatives of 1,4,8,11,15,18,22,25-octa(heptyloxymethyl)phthalocyanine were also prepared. Examples of the macrocycles were characterised using 1H NMR spectrometry and optical spectroscopy. Those bearing straight chains aggregate in solutions of chloroform and toluene. The octa(butoxymethyl)phthalocyanine and its longer chain homologues exhibit a discotic liquid crystallinephase. Compounds containing branched sidechains are liquid crystals at room temperature.",

author = "Cammidge, {Andrew N.} and Cook, {Michael J.} and Harrison, {Kenneth J.} and McKeown, {Neil B.}",

year = "1991",

doi = "10.1039/P19910003053",

language = "English",

pages = "3053--3058",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

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T1 - Synthesis and characterisation of some 1,4,8,11,15,18,22,25-octa(alkoxymethyl)phthalocyanines: A new series of discotic liquid crystals

AU - Cammidge, Andrew N.

AU - Cook, Michael J.

AU - Harrison, Kenneth J.

AU - McKeown, Neil B.

PY - 1991

Y1 - 1991

N2 - A series of 3, 6-bis(alkoxymethyl)phthalonitriles, prepared via Diels–Alder reactions of 2, 5-bis(alkoxymethyl)furans with fumaronitrile, have been converted into the corresponding phthalocyanines. Zn(II) and Cu(II) derivatives of 1,4,8,11,15,18,22,25-octa(heptyloxymethyl)phthalocyanine were also prepared. Examples of the macrocycles were characterised using 1H NMR spectrometry and optical spectroscopy. Those bearing straight chains aggregate in solutions of chloroform and toluene. The octa(butoxymethyl)phthalocyanine and its longer chain homologues exhibit a discotic liquid crystallinephase. Compounds containing branched sidechains are liquid crystals at room temperature.

AB - A series of 3, 6-bis(alkoxymethyl)phthalonitriles, prepared via Diels–Alder reactions of 2, 5-bis(alkoxymethyl)furans with fumaronitrile, have been converted into the corresponding phthalocyanines. Zn(II) and Cu(II) derivatives of 1,4,8,11,15,18,22,25-octa(heptyloxymethyl)phthalocyanine were also prepared. Examples of the macrocycles were characterised using 1H NMR spectrometry and optical spectroscopy. Those bearing straight chains aggregate in solutions of chloroform and toluene. The octa(butoxymethyl)phthalocyanine and its longer chain homologues exhibit a discotic liquid crystallinephase. Compounds containing branched sidechains are liquid crystals at room temperature.

U2 - 10.1039/P19910003053

DO - 10.1039/P19910003053

M3 - Article

SN - 1472-7781

SP - 3053

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

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