Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 30, Pages 6100-6109Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100891
Keywords
Cyanides; Fluorescence; Molecular devices; Viscosity; Density functional calculations
Categories
Funding
- Fundamental Research Funds for the Central Universities [DUT10ZD212, DUT11LK19]
- Royal Society (UK)
- NSFC China-UK Cost-Share Science Networks [21011130154]
- Ministry of Education [SRFDP-200801410004, NCET-08-0077]
- Education Department of Liaoning Province [2009 T015]
- State Key Laboratory of Fine Chemicals [KF0802]
- National Natural Science Foundation of China (NSFC) [20972024, 21073028]
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Fluorescent molecular rotors can be used as molecular sensors for the viscosity of a microenvironment. However, these molecular rotors are limited to 9-(dicyanovinyl) julolidine (DCVJ) and a few derivatives. Furthermore, these traditional rotors show short absorption/emission wavelengths and small Stokes shifts. To address these drawbacks, we have developed a small library of new molecular rotors for viscosity sensing, prepared by incorporating a thiophene unit into the conventional fluorescent molecular rotors with the aim of accessing molecular rotors with redshifted excitation/emission wavelengths and larger Stokes shifts compared with the known rotors. The new rotors show substantially improved photophysical properties. For example, rotor 4 shows absorption/emission wavelengths of 559/697 nm, respectively, and a very large Stokes shift of 138 nm compared with the absorption/emission wavelengths (465/503 nm) and very small Stokes shift (38 nm) of the traditional fluorescent molecular rotor DCVJ. The photophysical properties of the rotors were rationalized by DFT calculations.
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