Photophysical characterization of the 9,10-disubstituted anthracene chromophore and its applications in triplet-triplet annihilation photon upconversion
Journal article, 2015

Molecules based on anthracene are commonly used in applications such as OLEDs and triplet-triplet annihilation upconversion. In future design of blue emitting materials it is useful to know which part of the molecule can be altered in order to obtain new physical properties without losing the inherent optical properties. We have studied the effect of substitution of 9,10-substituted anthracenes. Eight anthracenes with aromatic phenyl and thiophene substituents were synthesised, containing both electron donating and accepting groups. The substitutions were found to affect the UV/Vis absorption only to a small extent, however the fluorescence properties were more affected with the thiophene substituents that decreased the fluorescence quantum yield from unity to <10%. DFT calculations confirm the minor change in absorption and indicate that the first and second triplet state energies are also unaffected. Finally the three most fluorescent derivatives 4-(10-phenylanthracene-9-yl) pyridine, 9-phenyl-10-(4-(trifluoromethyl)phenyl) anthracene and 4-(10-phenylanthracene-9-yl) benzonitrile were successfully utilized as annihilators in a triplet-triplet annihilation upconversion (TTA-UC) system employing platinum octaethylporphyrin as the sensitizer. The observed upconversion quantum yields, phi(UC), slightly exceeded that of the benchmark annihilator 9,10-diphenylanthracene (DPA).

power

gaussian-type basis

molecular-orbital methods

silicon solar-cells

delayed fluorescence

substituted anthracenes

organic-molecules

derivatives

visible-light

energy-transfer

Author

Victor Gray

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Damir Dzebo

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Angelica Lundin

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

J. Alborzpour

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Maria Abrahamsson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Bo Albinsson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Kasper Moth-Poulsen

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Journal of Materials Chemistry C

20507534 (ISSN) 20507526 (eISSN)

Vol. 3 42 11111-11121

Areas of Advance

Nanoscience and Nanotechnology (2010-2017)

Energy

Materials Science

Subject Categories

Materials Engineering

Chemical Sciences

Roots

Basic sciences

DOI

10.1039/c5tc02626a

More information

Latest update

11/23/2018