Photochromic anthracene systems containing hydrogen bonding sites
Lead Research Organisation:
University of Birmingham
Department Name: School of Chemistry
Abstract
The work will involve the synthesis and study of a series of receptor compounds that can bind charged or neutral organic compounds through hydrogen bonding interactions. The receptors will contain appropriate recognition motifs (crown ethers, amidopyridine units etc.) for binding barbiturates, imides, DNA strands and amino acid derivatives. These compounds and/or their hydrogen-bonded complexes will each contain two anthracene units to enable them to undergo reversible photodimerisation reactions. Detailed studies will be carried out on these photochromic systems using a variety of spectroscopic and analytical techniques. It is expected that both the efficiency of photodimerisation (the closing process) and the rate of the reverse reaction (the opening process) will be strongly affected by complex formation. Receptor synthesis (apart from DNA synthesis) and complexation studies (titrations and Job plots using NMR spectroscopy) will be carried out in Exeter by a PDRA. Detailed photophysical (UV/vis and fluorescence spectroscopy) and photochemical studies (reaction quantum yields) will be carried out by the PDRA in Bordeaux.
Publications
Darcos V
(2009)
Shining light on supramolecular assemblies
in Pure and Applied Chemistry
Liang CK
(2013)
Reversible control over molecular recognition in surface-bound photoswitchable hydrogen-bonding receptors: towards read-write-erase molecular printboards.
in Chemistry (Weinheim an der Bergstrasse, Germany)
Molard Y
(2006)
Structural effects on the ground and excited-state properties of photoswitchable hydrogen-bonding receptors.
in The Journal of organic chemistry
Description | Photochromism is the process by which certain organic molecules can change their shape in a reversible manner upon irradiation with light. Photochromic molecules can be attached to supramolecular receptors so that light can control receptor binding affinities, for example the binding towards metal cations. The challenge for this project was to explore whether binding towards organic molecules, in particular those that interact through H-bonding interactions, could be controlled by light. |
Exploitation Route | Nanoscale molecular devices. Nanoscale devices that can be controlled using external inputs such as light. |
Sectors | Chemicals |
Description | EPSRC Leadership Fellowship |
Amount | £1,727,390 (GBP) |
Funding ID | EP/G007578/1 |
Organisation | Engineering and Physical Sciences Research Council (EPSRC) |
Sector | Public |
Country | United Kingdom |
Start | 04/2009 |
End | 03/2014 |
Description | Collaboration with the University of Bordeaux |
Organisation | University of Bordeaux |
Department | Institute of Molecular Sciences (ISM) |
Country | France |
Sector | Academic/University |
PI Contribution | We supplied samples to the research team in Bordeaux for photophysical measurements. The collaborators are Dario Bassani and Nathan McClenaghan. |
Collaborator Contribution | The research team in Bordeaux carried out photo physical measurements on anthracene-containing samples. These have included supramolecular receptors and also DNA systems (for the EPSRC Leadership Fellowship). |
Impact | 1. Photocontrolled Binding and Binding-Controlled Photochromism within Anthracene-Modified DNA PIs: Bassani, DM; Tucker, JHR, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134, 10791-10794 2. Detection of DNA base variation and cytosine methylation at a single nucleotide site using a highly sensitive fluorescent probe PIs: Bassani, DM; Tucker, JHR, CHEMICAL COMMUNICATIONS, 2011, 47, 6629-6631 3. Anthracene-modified oligonucleotides as fluorescent DNA mismatch sensors: discrimination between various base-pair mismatches PIs: Bassani, DM; Tucker, JHR, SUPRAMOLECULAR CHEMISTRY, 2011, 23, 273-277 4. Structural effects on the ground and excited-state properties of photoswitchable hydrogen-bonding receptors PIs: Bassani, DM; Tucker, JHR, JOURNAL OF ORGANIC CHEMISTRY, 2006, 71, 8523-8531 5. Photorelease of an organic molecule in solution: Light-triggered blockage of a hydrogen-bonding receptor site PIs: Bassani, DM; Tucker, JHR, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44, 1072-1075 One further manuscript is in preparation and more may follow. Other recent pieces of work not directly linked to specific EPSRC grants are as follows: Detection of a single DNA base-pair mismatch using an anthracene-tagged fluorescent probe PIs: Bassani, DM; Tucker, JHR, CHEMICAL COMMUNICATIONS, 2006, 5003-5005 Reversible Control over Molecular Recognition in Surface-Bound Photoswitchable Hydrogen-Bonding Receptors: Towards Read-Write-Erase Molecular Printboards PIs: Tucker, JHR; Bassani, DM CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19, 12748-12758 Formation of a Hydrogen-Bonded Barbiturate [2]-Rotaxane PIs: Tucker, JHR; McClenaghan, ND, ORGANIC LETTERS, 2014, 16, 1358-1361 |
Start Year | 2006 |