Designing functionalized porphyrins capable of pseudo-2D self-assembly on surfaces

Sheshanath V. Bhosale; Mark A. Bissett; Craig Forsyth; Steven J. Langford; Suzanne M. Neville; Joseph G. Shapter; Laura Weeks; Clint P. Woodward

doi:10.1021/ol800895q

Designing functionalized porphyrins capable of pseudo-2D self-assembly on surfaces

Sheshanath V. Bhosale, Mark A. Bissett, Craig Forsyth, Steven J. Langford, Suzanne M. Neville, Joseph G. Shapter, Laura Weeks, Clint P. Woodward

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

Abstract

(Figure Presented) A crystallography-instructed strategy to highly ordered layering of porphyrins with different topologies on HOPG is developed based on meso-tetraarylporphyrins bearing 2-ethoxyethanol side chains as "sticky ends". These sticky ends are capable of displaying directive hydrogen bonding motifs with the inherent D4h symmetry of the porphyrins. Solvent effects are shown to have an important role in fabricating the adsorption. Metalation and subsequent axial ligation was a key controlling factor in the topology of the layer, leading to pseudo-2D structures on HOPG. © 2008 American Chemical Society.

Original language	English
Pages (from-to)	2943-2946
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	14
DOIs	https://doi.org/10.1021/ol800895q
Publication status	Published - 2008

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10.1021/ol800895q

CCDC 664957: Experimental Crystal Structure Determination
Bhosale, S. V. (Contributor), Bissett, M. (Contributor), Forsyth, C. (Contributor), Langford, S. J. (Contributor), Neville, S. M. (Contributor), Shapter, J. (Contributor), Weeks, L. (Contributor) & Woodward, C. P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2009
DOI: 10.5517/ccq9y75, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccq9y75&sid=DataCite
Dataset
CCDC 664958: Experimental Crystal Structure Determination
Bhosale, S. V. (Contributor), Bissett, M. (Contributor), Forsyth, C. (Contributor), Langford, S. J. (Contributor), Neville, S. M. (Contributor), Shapter, J. (Contributor), Weeks, L. (Contributor) & Woodward, C. P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2009
DOI: 10.5517/ccq9y86, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccq9y86&sid=DataCite
Dataset

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@article{32ed525f104f45a79630f4829e993e9f,

title = "Designing functionalized porphyrins capable of pseudo-2D self-assembly on surfaces",

abstract = "(Figure Presented) A crystallography-instructed strategy to highly ordered layering of porphyrins with different topologies on HOPG is developed based on meso-tetraarylporphyrins bearing 2-ethoxyethanol side chains as {"}sticky ends{"}. These sticky ends are capable of displaying directive hydrogen bonding motifs with the inherent D4h symmetry of the porphyrins. Solvent effects are shown to have an important role in fabricating the adsorption. Metalation and subsequent axial ligation was a key controlling factor in the topology of the layer, leading to pseudo-2D structures on HOPG. {\textcopyright} 2008 American Chemical Society.",

author = "Bhosale, {Sheshanath V.} and Bissett, {Mark A.} and Craig Forsyth and Langford, {Steven J.} and Neville, {Suzanne M.} and Shapter, {Joseph G.} and Laura Weeks and Woodward, {Clint P.}",

year = "2008",

doi = "10.1021/ol800895q",

language = "English",

volume = "10",

pages = "2943--2946",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Designing functionalized porphyrins capable of pseudo-2D self-assembly on surfaces

AU - Bhosale, Sheshanath V.

AU - Bissett, Mark A.

AU - Forsyth, Craig

AU - Langford, Steven J.

AU - Neville, Suzanne M.

AU - Shapter, Joseph G.

AU - Weeks, Laura

AU - Woodward, Clint P.

PY - 2008

Y1 - 2008

N2 - (Figure Presented) A crystallography-instructed strategy to highly ordered layering of porphyrins with different topologies on HOPG is developed based on meso-tetraarylporphyrins bearing 2-ethoxyethanol side chains as "sticky ends". These sticky ends are capable of displaying directive hydrogen bonding motifs with the inherent D4h symmetry of the porphyrins. Solvent effects are shown to have an important role in fabricating the adsorption. Metalation and subsequent axial ligation was a key controlling factor in the topology of the layer, leading to pseudo-2D structures on HOPG. © 2008 American Chemical Society.

AB - (Figure Presented) A crystallography-instructed strategy to highly ordered layering of porphyrins with different topologies on HOPG is developed based on meso-tetraarylporphyrins bearing 2-ethoxyethanol side chains as "sticky ends". These sticky ends are capable of displaying directive hydrogen bonding motifs with the inherent D4h symmetry of the porphyrins. Solvent effects are shown to have an important role in fabricating the adsorption. Metalation and subsequent axial ligation was a key controlling factor in the topology of the layer, leading to pseudo-2D structures on HOPG. © 2008 American Chemical Society.

U2 - 10.1021/ol800895q

DO - 10.1021/ol800895q

M3 - Article

SN - 1523-7052

VL - 10

SP - 2943

EP - 2946

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Designing functionalized porphyrins capable of pseudo-2D self-assembly on surfaces

Abstract

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Datasets

CCDC 664957: Experimental Crystal Structure Determination

CCDC 664958: Experimental Crystal Structure Determination

Cite this