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Synthesis of a Novel Spiropyran for the Non-Covalent Functionalisation of Single-Walled Carbon Nanotubes

Synthesis of a Novel Spiropyran for the Non-Covalent Functionalisation of Single-Walled Carbon Nanotubes

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An essay for the 2011 Undergraduate Awards (Lecturer Nomination) Competition by Fergus Poynton. It is nominated by Lecturer Sylvia Draper of Trinity College, University of Dublin in the category of Physical Sciences
An essay for the 2011 Undergraduate Awards (Lecturer Nomination) Competition by Fergus Poynton. It is nominated by Lecturer Sylvia Draper of Trinity College, University of Dublin in the category of Physical Sciences

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Published by: Undergraduate Awards on Sep 01, 2012
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10/27/2013

 
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Synthesis of a Novel Spiropyran for the Non-CovalentFunctionalisation of Single-Walled Carbon Nanotubes
 
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1. Introduction
1.1 Aims
The main aim of this research project is to provide essential information in the developmentof a nano-sized smart material constituted by single-walled carbon nanotubes (SWNTs) non-covalently functionalised with a photoswitchable molecule (spiropyran). In this context, thefollowing goals have been achieved:
 
Synthesis of a newly designed spiropyran derivative (called
SP-Chain
) coupled withan aliphatic chain;
 
Optical characterisation of the photochromic behaviour of 
SP-Chain
;
 
Non-covalent functionalisation of SWNTs with
SP-Chain
;
 
Characterisation of the photochromic switching of the supramolecular conjugate.
1.2 Molecular Switches
Molecular switches are molecules which can be converted between two different isomericstates by the application of external stimuli (e.g. light or temperature). For this reason they canbe integrated in functional devices or materials that allow the modulation of numerous propertiesof such composites (
Figure 1
).
1
 
Figure 1
: Example of molecular switches incorporated in a functionaldevice.
2
 
 
3
As their individual effects can be quite small in relation to the large system into which theycan be incorporated, they demonstrate a novel way to amplify initial switching across the wholedevice. For example, incorporation of a switch into the side chains of a polypeptide allows theamplification of the switch’s signal as it induces conformational changes in the macromolecularstructure of the polypeptide upon activation or deactivation of the switch.
3,4
 There are a number of mechanisms by which different types of molecular switches operateincluding: photoinduced electron transfer, the optical control of chirality and photochromism.The latter is the mechanism of action of the molecular switch employed in this report. In light-responsive (photochromic) molecular switches the chromophoric moiety of the molecule isresponsible for the absorption of light, which leads to the promotion of the molecule to anelectronic excited state from where the reaction pathway continues to produce a fluorescentsignal. There are three main characteristics for highly efficient photochromic molecules: i) alarge ground state extinction coefficient
,
ii) a reasonably long excited-state lifetime (severalnanoseconds), and iii) a high-fluorescent-quantum-yield-to-minimise-side-reactions.
5
 
1.3 Photochromism
Photochromism is the reversible transformation of a chemical species between two isomers,each with different absorption spectra, which is induced in at least one direction by theabsorption of electromagnetic radiation.
6
The reverse reaction can occur photochemically orthermally where the prefixes
P-
and
T-type
indicate the respective pathways which the moleculefollows.
6
Indeed photochromic systems have been used for thousands of years: for example,human vision relies on the photochromic proteins rhodopsin and iodopsin, which are located inthe retina of the eye.
7-9
The first observations of photochromism in solution were reported by

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