Synthesis of meso-substituted subphthalocyanine-subporphyrin hybrids: Boron subtribenzodiazaporphyrins

Sonia Remiro Buenamanana; Alejandro Diaz-Moscoso; David Hughes; Manfred Bochmann; Graham J. Tizzard; Simon J. Coles; Andy Cammidge

doi:10.1002/anie.201502662

Synthesis of meso-substituted subphthalocyanine-subporphyrin hybrids: Boron subtribenzodiazaporphyrins

Sonia Remiro Buenamanana, Alejandro Diaz-Moscoso, David Hughes, Manfred Bochmann, Graham J. Tizzard, Simon J. Coles, Andy Cammidge

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

22 Citations (Scopus)

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Abstract

The first syntheses of hybrid structures that lie between SubPhthalocyanines and SubPorphyrins are reported. The versatile, single-step synthetic protocol uses a preformed aminoisoindolene to provide the bridging methine unit and its substituent, while trialkoxyborates simultaneously act as Lewis acid/template and provider of the apical substituent. Selection of each component therefore allows controlled formation of diverse, differentially functionalised systems. The new hybrids are isolated as robust, pure materials that display intense absorption and emission in the mid-visible region. They are further characterised in solution and solid state by variable temperature NMR spectroscopy and X-ray crystallography respectively

Original language	English
Pages (from-to)	7510-7514
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	54
Issue number	26
DOIs	https://doi.org/10.1002/anie.201502662
Publication status	Published - 22 Jun 2015

Keywords

dyes/pigments
heterocycles
phthalocyanines
porphyrinoids
synthetic methods

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10.1002/anie.201502662

Remiro_Buenamaana_et_al-2015-Angewandte_Chemie_International_EditionFinal published version, 2.7 MB

Manfred Bochmann
- M.Bochmannuea.acuk
- School of Chemistry, Pharmacy and Pharmacology - Emeritus Professor
- Chemistry of Light and Energy - Member
- Chemistry of Materials and Catalysis - Member
Person: Honorary, Research Group Member
Andy Cammidge
- A.Cammidgeuea.acuk
- School of Chemistry, Pharmacy and Pharmacology - Professor of Chemistry
- Centre for Photonics and Quantum Science - Member
- Chemistry of Light and Energy - Member
- Chemistry of Materials and Catalysis - Member
Person: Research Group Member, Academic, Teaching & Research

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title = "Synthesis of meso-substituted subphthalocyanine-subporphyrin hybrids: Boron subtribenzodiazaporphyrins",

abstract = "The first syntheses of hybrid structures that lie between SubPhthalocyanines and SubPorphyrins are reported. The versatile, single-step synthetic protocol uses a preformed aminoisoindolene to provide the bridging methine unit and its substituent, while trialkoxyborates simultaneously act as Lewis acid/template and provider of the apical substituent. Selection of each component therefore allows controlled formation of diverse, differentially functionalised systems. The new hybrids are isolated as robust, pure materials that display intense absorption and emission in the mid-visible region. They are further characterised in solution and solid state by variable temperature NMR spectroscopy and X-ray crystallography respectively",

keywords = "dyes/pigments, heterocycles, phthalocyanines, porphyrinoids, synthetic methods",

author = "{Remiro Buenamanana}, Sonia and Alejandro Diaz-Moscoso and David Hughes and Manfred Bochmann and Tizzard, {Graham J.} and Coles, {Simon J.} and Andy Cammidge",

year = "2015",

month = jun,

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doi = "10.1002/anie.201502662",

language = "English",

volume = "54",

pages = "7510--7514",

journal = "Angewandte Chemie-International Edition",

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publisher = "Wiley",

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T1 - Synthesis of meso-substituted subphthalocyanine-subporphyrin hybrids: Boron subtribenzodiazaporphyrins

AU - Remiro Buenamanana, Sonia

AU - Diaz-Moscoso, Alejandro

AU - Hughes, David

AU - Bochmann, Manfred

AU - Tizzard, Graham J.

AU - Coles, Simon J.

AU - Cammidge, Andy

PY - 2015/6/22

Y1 - 2015/6/22

N2 - The first syntheses of hybrid structures that lie between SubPhthalocyanines and SubPorphyrins are reported. The versatile, single-step synthetic protocol uses a preformed aminoisoindolene to provide the bridging methine unit and its substituent, while trialkoxyborates simultaneously act as Lewis acid/template and provider of the apical substituent. Selection of each component therefore allows controlled formation of diverse, differentially functionalised systems. The new hybrids are isolated as robust, pure materials that display intense absorption and emission in the mid-visible region. They are further characterised in solution and solid state by variable temperature NMR spectroscopy and X-ray crystallography respectively

AB - The first syntheses of hybrid structures that lie between SubPhthalocyanines and SubPorphyrins are reported. The versatile, single-step synthetic protocol uses a preformed aminoisoindolene to provide the bridging methine unit and its substituent, while trialkoxyborates simultaneously act as Lewis acid/template and provider of the apical substituent. Selection of each component therefore allows controlled formation of diverse, differentially functionalised systems. The new hybrids are isolated as robust, pure materials that display intense absorption and emission in the mid-visible region. They are further characterised in solution and solid state by variable temperature NMR spectroscopy and X-ray crystallography respectively

KW - dyes/pigments

KW - heterocycles

KW - phthalocyanines

KW - porphyrinoids

KW - synthetic methods

U2 - 10.1002/anie.201502662

DO - 10.1002/anie.201502662

M3 - Article

VL - 54

SP - 7510

EP - 7514

JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

SN - 1433-7851

IS - 26

ER -

Synthesis of meso-substituted subphthalocyanine-subporphyrin hybrids: Boron subtribenzodiazaporphyrins

Abstract

Keywords

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Manfred Bochmann

Andy Cammidge

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