Synthesis and self-assembling behavior of a porphyrin bearing multiple meso-conjugated barbiturates

Satoshi Arai; Toshiya Okamura; Shinji Takeoka

doi:10.1016/j.tetlet.2010.07.139

Synthesis and self-assembling behavior of a porphyrin bearing multiple meso-conjugated barbiturates

Satoshi Arai, Toshiya Okamura, Shinji Takeoka

School of Advanced Science and Engineering

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

2 Citations (Scopus)

Abstract

An efficient procedure through deprotection of 2,4,6-trimethoxypyrimidine derivative afforded porphyrinato zinc bearing multi-barbiturates acting as multiple hydrogen bonding sites at the meso positions. Addition of excess amphiphilic triaminopyrimidine derivative, as a complementary motif to the barbiturate, in an aqueous solution of porphyrin conjugated with multiple barbiturates at the meso positions resulted in precipitation. The cast film from the chloroform solution of the precipitate indicated the formation of a well-defined porphyrin assembly.

Original language	English
Pages (from-to)	5177-5180
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2010.07.139
Publication status	Published - 2010 Sep 29

Keywords

Barbituric acid
Hydrogen bonding
Porphyrin
Self-assembly

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis and self-assembling behavior of a porphyrin bearing multiple meso-conjugated barbiturates",

abstract = "An efficient procedure through deprotection of 2,4,6-trimethoxypyrimidine derivative afforded porphyrinato zinc bearing multi-barbiturates acting as multiple hydrogen bonding sites at the meso positions. Addition of excess amphiphilic triaminopyrimidine derivative, as a complementary motif to the barbiturate, in an aqueous solution of porphyrin conjugated with multiple barbiturates at the meso positions resulted in precipitation. The cast film from the chloroform solution of the precipitate indicated the formation of a well-defined porphyrin assembly.",

keywords = "Barbituric acid, Hydrogen bonding, Porphyrin, Self-assembly",

author = "Satoshi Arai and Toshiya Okamura and Shinji Takeoka",

note = "Funding Information: This work was supported in part by the {\textquoteleft}High-Tech Research Center{\textquoteright} Project for Waseda University: matching fund subsidy, Global COE {\textquoteleft}Practical Chemical Wisdom{\textquoteright}. The author thank Dr. Shinsuke Ishihara for helpful discussion about X-ray and polarized microscope observation. ",

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T1 - Synthesis and self-assembling behavior of a porphyrin bearing multiple meso-conjugated barbiturates

AU - Arai, Satoshi

AU - Okamura, Toshiya

AU - Takeoka, Shinji

N1 - Funding Information: This work was supported in part by the ‘High-Tech Research Center’ Project for Waseda University: matching fund subsidy, Global COE ‘Practical Chemical Wisdom’. The author thank Dr. Shinsuke Ishihara for helpful discussion about X-ray and polarized microscope observation.

PY - 2010/9/29

Y1 - 2010/9/29

N2 - An efficient procedure through deprotection of 2,4,6-trimethoxypyrimidine derivative afforded porphyrinato zinc bearing multi-barbiturates acting as multiple hydrogen bonding sites at the meso positions. Addition of excess amphiphilic triaminopyrimidine derivative, as a complementary motif to the barbiturate, in an aqueous solution of porphyrin conjugated with multiple barbiturates at the meso positions resulted in precipitation. The cast film from the chloroform solution of the precipitate indicated the formation of a well-defined porphyrin assembly.

AB - An efficient procedure through deprotection of 2,4,6-trimethoxypyrimidine derivative afforded porphyrinato zinc bearing multi-barbiturates acting as multiple hydrogen bonding sites at the meso positions. Addition of excess amphiphilic triaminopyrimidine derivative, as a complementary motif to the barbiturate, in an aqueous solution of porphyrin conjugated with multiple barbiturates at the meso positions resulted in precipitation. The cast film from the chloroform solution of the precipitate indicated the formation of a well-defined porphyrin assembly.

KW - Barbituric acid

KW - Hydrogen bonding

KW - Porphyrin

KW - Self-assembly

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JO - Tetrahedron Letters

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SN - 0040-4039

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Synthesis and self-assembling behavior of a porphyrin bearing multiple meso-conjugated barbiturates

Abstract

Keywords

ASJC Scopus subject areas

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