Positional selectivity of reversible azomethine condensation reactions at solid/liquid interfaces leading to supramolecule formation

Ryota Tanoue; Rintaro Higuchi; Kiryu Ikebe; Shinobu Uemura; Nobuo Kimizuka; Adam Z. Stieg; James K. Gimzewski; Masashi Kunitake

doi:10.1016/j.jelechem.2013.11.022

Positional selectivity of reversible azomethine condensation reactions at solid/liquid interfaces leading to supramolecule formation

Ryota Tanoue
, Rintaro Higuchi
, Kiryu Ikebe
, Shinobu Uemura
, Nobuo Kimizuka
, Adam Z. Stieg
, James K. Gimzewski
, Masashi Kunitake

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

13 Citations (Scopus)

Abstract

We used in situ scanning tunneling microscopy to investigate the formation of two-dimensional supramolecules by means of reversible azomethine condensation reactions between aqueous 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAPP) and terephthaldicarboxaldehyde (TPA) or benzaldehyde (BA) at the solid/liquid interface of an iodine-modified Au(1 1 1) surface. A nanomesh and a close-packed array were formed by the reaction of TAPP with the dicarboxaldehyde. Formation of these structures was driven by Schiff base (azomethine) bonding and simultaneous self-assembly controlled by adsorption and condensation equilibria. Surface cross coupling between TAPP and the monocarboxaldehyde (BA) formed highly ordered adlayers consisting solely of TAPP symmetrically disubstituted with two BA molecules attached at diagonally opposite corners. The position selectivity was achieved through simultaneous coupling reaction equilibria and the thermodynamic self-assembly.

Original language	English
Pages (from-to)	145-149
Number of pages	5
Journal	Journal of Electroanalytical Chemistry
Volume	716
DOIs	https://doi.org/10.1016/j.jelechem.2013.11.022
Publication status	Published - Mar 1 2014

All Science Journal Classification (ASJC) codes

Analytical Chemistry
General Chemical Engineering
Electrochemistry

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10.1016/j.jelechem.2013.11.022

Cite this

@article{2efae55c0da243268795cb9b570948ac,

title = "Positional selectivity of reversible azomethine condensation reactions at solid/liquid interfaces leading to supramolecule formation",

abstract = "We used in situ scanning tunneling microscopy to investigate the formation of two-dimensional supramolecules by means of reversible azomethine condensation reactions between aqueous 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAPP) and terephthaldicarboxaldehyde (TPA) or benzaldehyde (BA) at the solid/liquid interface of an iodine-modified Au(1 1 1) surface. A nanomesh and a close-packed array were formed by the reaction of TAPP with the dicarboxaldehyde. Formation of these structures was driven by Schiff base (azomethine) bonding and simultaneous self-assembly controlled by adsorption and condensation equilibria. Surface cross coupling between TAPP and the monocarboxaldehyde (BA) formed highly ordered adlayers consisting solely of TAPP symmetrically disubstituted with two BA molecules attached at diagonally opposite corners. The position selectivity was achieved through simultaneous coupling reaction equilibria and the thermodynamic self-assembly.",

author = "Ryota Tanoue and Rintaro Higuchi and Kiryu Ikebe and Shinobu Uemura and Nobuo Kimizuka and Stieg, \{Adam Z.\} and Gimzewski, \{James K.\} and Masashi Kunitake",

note = "Funding Information: We greatly appreciate the contributions of Professor Kingo Itaya, who is a pioneer in this field. Our work was partially supported by Core Research for Evolutional Science and Technology of the Japan Science and Technology Agency and a Grant-in-Aid for Scientific Research on Innovative Areas “New Polymeric Materials Based on Element-Blocks” ( 24102006 ) from the Ministry of Education, Culture, Sports, Science and Technology, Japan . R.T. thanks the Japan Society for the Promotion of Science for a research fellowship. This paper is dedicated to the memory of Dr. Heinrich Rohrer. ",

year = "2014",

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doi = "10.1016/j.jelechem.2013.11.022",

language = "English",

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T1 - Positional selectivity of reversible azomethine condensation reactions at solid/liquid interfaces leading to supramolecule formation

AU - Tanoue, Ryota

AU - Higuchi, Rintaro

AU - Ikebe, Kiryu

AU - Uemura, Shinobu

AU - Kimizuka, Nobuo

AU - Stieg, Adam Z.

AU - Gimzewski, James K.

AU - Kunitake, Masashi

N1 - Funding Information: We greatly appreciate the contributions of Professor Kingo Itaya, who is a pioneer in this field. Our work was partially supported by Core Research for Evolutional Science and Technology of the Japan Science and Technology Agency and a Grant-in-Aid for Scientific Research on Innovative Areas “New Polymeric Materials Based on Element-Blocks” ( 24102006 ) from the Ministry of Education, Culture, Sports, Science and Technology, Japan . R.T. thanks the Japan Society for the Promotion of Science for a research fellowship. This paper is dedicated to the memory of Dr. Heinrich Rohrer.

PY - 2014/3/1

Y1 - 2014/3/1

N2 - We used in situ scanning tunneling microscopy to investigate the formation of two-dimensional supramolecules by means of reversible azomethine condensation reactions between aqueous 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAPP) and terephthaldicarboxaldehyde (TPA) or benzaldehyde (BA) at the solid/liquid interface of an iodine-modified Au(1 1 1) surface. A nanomesh and a close-packed array were formed by the reaction of TAPP with the dicarboxaldehyde. Formation of these structures was driven by Schiff base (azomethine) bonding and simultaneous self-assembly controlled by adsorption and condensation equilibria. Surface cross coupling between TAPP and the monocarboxaldehyde (BA) formed highly ordered adlayers consisting solely of TAPP symmetrically disubstituted with two BA molecules attached at diagonally opposite corners. The position selectivity was achieved through simultaneous coupling reaction equilibria and the thermodynamic self-assembly.

AB - We used in situ scanning tunneling microscopy to investigate the formation of two-dimensional supramolecules by means of reversible azomethine condensation reactions between aqueous 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAPP) and terephthaldicarboxaldehyde (TPA) or benzaldehyde (BA) at the solid/liquid interface of an iodine-modified Au(1 1 1) surface. A nanomesh and a close-packed array were formed by the reaction of TAPP with the dicarboxaldehyde. Formation of these structures was driven by Schiff base (azomethine) bonding and simultaneous self-assembly controlled by adsorption and condensation equilibria. Surface cross coupling between TAPP and the monocarboxaldehyde (BA) formed highly ordered adlayers consisting solely of TAPP symmetrically disubstituted with two BA molecules attached at diagonally opposite corners. The position selectivity was achieved through simultaneous coupling reaction equilibria and the thermodynamic self-assembly.

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U2 - 10.1016/j.jelechem.2013.11.022

DO - 10.1016/j.jelechem.2013.11.022

M3 - Article

AN - SCOPUS:84897991424

SN - 1572-6657

VL - 716

SP - 145

EP - 149

JO - Journal of Electroanalytical Chemistry

JF - Journal of Electroanalytical Chemistry

ER -

Positional selectivity of reversible azomethine condensation reactions at solid/liquid interfaces leading to supramolecule formation

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