Table Of ContentCHEMISTRY RESEARCH AND APPLICATIONS
C C
LICK HEMISTRY
A , A
PPROACHES PPLICATIONS
C
AND HALLENGES
No part of this digital document may be reproduced, stored in a retrieval system or transmitted in any form or
by any means. The publisher has taken reasonable care in the preparation of this digital document, but makes no
expressed or implied warranty of any kind and assumes no responsibility for any errors or omissions. No
liability is assumed for incidental or consequential damages in connection with or arising out of information
contained herein. This digital document is sold with the clear understanding that the publisher is not engaged in
rendering legal, medical or any other professional services.
C R
HEMISTRY ESEARCH
A
AND PPLICATIONS
Additional books in this series can be found on Nova’s website
under the Series tab.
Additional e-books in this series can be found on Nova’s website
under the eBooks tab.
CHEMISTRY RESEARCH AND APPLICATIONS
C C
LICK HEMISTRY
A , A
PPROACHES PPLICATIONS AND
C
HALLENGES
YU CHEN
AND
ZONG-RUI TONG
EDITORS
Copyright © 2017 by Nova Science Publishers, Inc.
All rights reserved. No part of this book may be reproduced, stored in a retrieval system or transmitted in any form
or by any means: electronic, electrostatic, magnetic, tape, mechanical photocopying, recording or otherwise without
the written permission of the Publisher.
We have partnered with Copyright Clearance Center to make it easy for you to obtain permissions to reuse content
from this publication. Simply navigate to this publication’s page on Nova’s website and locate the “Get Permission”
button below the title description. This button is linked directly to the title’s permission page on copyright.com.
Alternatively, you can visit copyright.com and search by title, ISBN, or ISSN.
For further questions about using the service on copyright.com, please contact:
Copyright Clearance Center
Phone: +1-(978) 750-8400 Fax: +1-(978) 750-4470 E-mail: [email protected].
NOTICE TO THE READER
The Publisher has taken reasonable care in the preparation of this book, but makes no expressed or implied
warranty of any kind and assumes no responsibility for any errors or omissions. No liability is assumed for
incidental or consequential damages in connection with or arising out of information contained in this book.
The Publisher shall not be liable for any special, consequential, or exemplary damages resulting, in whole or
in part, from the readers’ use of, or reliance upon, this material. Any parts of this book based on government
reports are so indicated and copyright is claimed for those parts to the extent applicable to compilations of
such works.
Independent verification should be sought for any data, advice or recommendations contained in this book. In
addition, no responsibility is assumed by the publisher for any injury and/or damage to persons or property
arising from any methods, products, instructions, ideas or otherwise contained in this publication.
This publication is designed to provide accurate and authoritative information with regard to the subject
matter covered herein. It is sold with the clear understanding that the Publisher is not engaged in rendering
legal or any other professional services. If legal or any other expert assistance is required, the services of a
competent person should be sought. FROM A DECLARATION OF PARTICIPANTS JOINTLY ADOPTED
BY A COMMITTEE OF THE AMERICAN BAR ASSOCIATION AND A COMMITTEE OF
PUBLISHERS.
Additional color graphics may be available in the e-book version of this book.
Library of Congress Cataloging-in-Publication Data
Names: Chen, Yu (Chemist), editor. | Tong, Zong-Rui, editor.
Title: Click chemistry : approaches, applications, and challenges / editors,
Yu Chen and Zong-Rui Tong (School of Material Science and
Engineering, Beijing Institute of Technology, Beijing, China, and others).
Description: Hauppauge, New York : Nova Science Publishers, Inc., [2017] |
Series: Chemistry research and applications | Includes index.
Identifiers: LCCN 2017017342 (print) | LCCN 2017018840 (ebook) | ISBN
9781536119237(cid:3)(cid:11)(cid:72)(cid:37)(cid:82)(cid:82)(cid:78)(cid:12) | ISBN 9781536119039 (hardcover)
Subjects: LCSH: Chemical equilibrium. | Chemical reactions. |
Biocompatibility.
Classification: LCC QD503 (ebook) | LCC QD503 .C565 2017 (print) | DDC
547/.2--dc23
LC record available at https://lccn.loc.gov/2017017342
Published by Nova Science Publishers, Inc. † New York
CONTENTS
Chapter 1 The Introduction of Click Chemistry Reaction 1
Yu Chen
Chapter 2 Nitrile N-Oxide-Based Click Reactions
Accompanying C-C Bond Formation 21
Yasuhito Koyama and Toshikazu Takata
Chapter 3 Bi-1,2,3-Triazoles: Synthesis and Perspectives 51
Ivette Santana-Martinez and Erick Cuevas-Yañez
Chapter 4 Click Chemistry of Natural Polymers 69
Yu-Tong Zhang, Zhu-Yun Li and Yu Chen
Chapter 5 Synthesis and Functionalization of Hydrogel through
“Click-Chemistry” 107
Mi-Heng Dong and Yu Chen
Chapter 6 Using of Click Chemistry for Elastomer 139
Ya-Lun Wang and Yu Chen
Chapter 7 Surface Engineering of Porous Monoliths via
Click Chemistry: Towards Functional Materials for
Flow Chemistry Applications 157
Seydina Ibrahima Kebe, Hela Kammoun,
Mohamed Guerrouache, Samia Mahouche-Chergui,
Sabrina Belbekhouche, Benjamin Le Droumaguet,
Yosra Dridi-Zrelli and Benjamin Carbonnier
vi Contents
Chapter 8 Click Chemistry for Membrane Preparation and
Surface Modification 211
Zhu-Fang Hu, Jin Zhou and Hai-Yin Yu
Chapter 9 Copper-Mediated Click Chemistry Applications to
Assemble Polyaromatic Structures 235
Celedonio M. Álvarez, Héctor Barbero and
Sergio Ferrero
Chapter 10 Application of Click Chemistry in Biomedical Fields 281
Yu Chen, Ying Zhang, Xiaoyu Sun and Jingjing Yuan
Chapter 11 Click Chemistry: Optical Sensing in
Biological Analysis 313
Suyan Qiu, Fang Luo, Linguang Luo, Longhua Guo,
Bin Qiu, Zhenyu Lin and Guonan Chen
Chapter 12 Telechilic Polybutadiene Solid Propellant Binders
Based on ‘Çlick’ Chemistry Approach 347
S. Reshmi, E. Arunan and C. P. Reghunadhan Nair
Editor Contact Information 367
Index 369
In: Click Chemistry ISBN: 978-1-53611-903-9
Editors: Y. Chen and Z. R. Tong ©2017 Nova Science Publishers, Inc.
Chapter 1
THE INTRODUCTION OF
CLICK CHEMISTRY REACTION
Yu Chen*
School of Materials Science and Engineering,
Beijing Institute of Technology, Beijing, China
ABSTRACT
Click chemistry, which is also called as linkage chemistry, dynamic,
combinatorial chemistry or quick linking combinatorial chemistry,
describes the reaction that joins molecular fragments as simple, efficient
and versatile as clicking a mouse. The two units with specific click
structures can be linked by click reaction, no matter what is attached to
the structure and only the specific click structures can be joined. It
emphasizes the development of new combinatorial chemistries on the
basis of the synthesis of efficient and highly selective carbon-heteroatom
bond (C-X-C) and effectively prepares molecules with high diversity by
these simple reactions. It significantly simplified and promoted the
development of synthesis chemistry. Click chemistry has become one of
the most useful and attractive synthetic strategy in many fields. In the
current chapter, the definition of the click chemistry was explained, the
characteristics and types of the click chemistry was introduces, some
specific reaction types were focused. Application of click chemistry in
different fields and its development were briefly introduced. It is helpful
* Corresponding Author Email: [email protected].
2 Yu Chen
for the whole comprehension of the readers to the characteristics and
development of this type reaction.
1. DEVELOPMENT OF CLICK CHEMISTRY
With the development of modern science and technology, the
conventional chemical synthesis cannot meet the demands on the rapid
synthesis a large number of target compounds. To overcome this challenge,
the “click chemistry” was proposed based on the synthesis of natural products
and biosynthesis pathways [1]. The nature can generate complicated biological
molecules, such as proteins and polysaccharides, by joining the modular
units of choice with specific biomolecules, such as amino acids and
monosaccharides. This process is characterized with obvious “modular”
features and can form carbon-heteroatom bonds between specific functional
groups, which connect amino acids and monosaccharides into various
biological molecules.
With the growth of the new drug demand and the development of high-
throughput screening since the late 20th century, the rapid synthesis of a large
number of new molecules has become an urgent task for organic synthesis
[2, 3]. Studies have been focused on constructing molecular libraries [4, 5],
developing molecular diversity [6] and meet the needs for synthesis of new
drugs [7]. The modern technologies and tools, such as chiral techniques, high-
throughput techniques, have significantly improved the quality of drug
chemical synthesis and promoted drug development.
A pharmaceutically-acceptable compound should consist of at least 30
non-hydrogen atoms with a molecular weight of no less than 500 Da [8]. It
should be composed of hydrogen, carbon, nitrogen, oxygen, phosphorous,
sulfur, chlorine and bromine and highly tolerant to oxygen and water at room
temperature [9]. In 1996, Guida et al. found by computer simulation that there
were as many as 1063 compounds meeting these criteria, which is one million
times of total atoms in the sun [10]. However, only 106 -107 known
compounds fulfill these criteria, indicating that only a small portion of drugs
have been developed largely due to the low efficiency of current synthesis
methods. Therefore, the development of reliable, high efficiency and highly
selective click reaction that follows the “modular” synthesis in nature would
have a revolutionary effect on the drug synthesis, as well as the development
and synthesis of other new materials [11].
The Introduction of Click Chemistry Reaction 3
In the past 150 years of modern chemistry history, a variety of synthesis
techniques have been developed to join molecular fragments. Many of them,
such as the “combinatorial chemistry” invented in the 1990s, are very delicate
and require careful manipulations of highly reactive reactants under very
restricted conditions. However, combinatorial chemistry relies on the reactions
between monomers more than traditional synthetic chemistry, which limits its
application in the synthesis of compounds of diverse structures.
In 1893, Michael et al. [12]. reported for the first time the azide-acetylenic
cycloaddition reaction under non-catalytic conditions. In the mid-late 20th
century, Huisgen et al. [13] established a new type of reaction, e.g., 1, 3-
dipolar cycloaddition via thorough mechanistic investigation and synthetic
application. However, such reaction under non-catalytic conditions requires
high reaction temperature (80-120℃) and long reaction time (12-24h). In 2001,
Meldal et al. [14] in Denmark and Sharpless et al. of Scripps Research
Institute in the United States independently discovered the copper catalyzed
azide-alkyne cycloaddition that could be completed in 8h at room temperature.
The reaction is easy to perform and produce target products quickly with high
yields and little or no by-products. It can be conducted under a variety
conditions, especially in water, without affected by the neighbor functional
groups. The reaction under the optimal conditions was named by the
researchers as “click chemistry” that could rapidly join small units to yield
various compounds. The core of this reaction is to generate heteroatom-
containing compounds by a series of reliable modular reactions. Click
chemistry fulfilled the requirements to the chemical synthesis of molecular
diversity. In 2001, Sharpless et al. was awarded the Nobel Prize in chemistry
for their pilot work in “click chemistry.”
Click chemistry can also be called as Linkage Chemistry, Dynamic,
Combinatorial Chemistry or Quick Linking Combinatorial Chemistry.
Click chemistry, also known as tagging, describes the reaction that joins
molecular fragments as simple, efficient and versatile as clicking a mouse. The
two units with specific click structures can be linked by click reaction, no
matter what is attached to the structure and only the specific click structures
can be joined. It emphasizes the development of new combinatorial
chemistries on the basis of the synthesis of efficient and highly selective
carbon-heteroatom bond (C-X-C) and effectively prepares molecules with high
diversity by these simple reactions [15, 16]. It significantly simplified and
promoted the development of synthesis chemistry. Click chemistry has
become one of the most useful and attractive synthetic strategy in many fields,
