Synthesis and Photoluminescent Properties of Geometrically Hindered cis-Tris(diphenylaminofluorene) as Precursors to Light-Emitting Devices

Nam-Goo Kang; Ken Kokubo; Seaho Jeon; Min Wang; Chang-Lyoul Lee; Taizoon Canteenwala; Loon-Seng Tan; Long Y. Chiang

doi:10.3390/molecules20034635

Molecules (Mar 2015)

Synthesis and Photoluminescent Properties of Geometrically Hindered cis-Tris(diphenylaminofluorene) as Precursors to Light-Emitting Devices

Nam-Goo Kang,
Ken Kokubo,
Seaho Jeon,
Min Wang,
Chang-Lyoul Lee,
Taizoon Canteenwala,
Loon-Seng Tan,
Long Y. Chiang

Affiliations

Nam-Goo Kang: Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA
Ken Kokubo: Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Seaho Jeon: Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA
Min Wang: Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA
Chang-Lyoul Lee: Advanced Photonics Research Institute, Gwangju Institute of Science and Technology, Gwangju 500–712, Korea
Taizoon Canteenwala: Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA
Loon-Seng Tan: AFRL/RXBN, Air Force Research Laboratory, Wright-Patterson Air Force Base, Dayton, OH 45433, USA
Long Y. Chiang: Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA

DOI: https://doi.org/10.3390/molecules20034635
Journal volume & issue: Vol. 20, no. 3
pp. 4635 – 4654

Abstract

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A novel highly luminescent tris-fluorenyl ring-interconnected chromophore tris(DPAF-C9) was synthesized using a C3 symmetrical triaminobenzene core as the synthon. This structure bears three light-harvesting 2-diphenylamino-9,9-dialkylfluorenyl (DPAF) ring moieties with each attached by two branched 3',5',5'-trimethylhexyl (C9) arms. A major stereoisomer was chromatographically isolated and characterized to possess a 3D structural configuration of cis-conformer in a cup-form. Molecular calculation at B3LYP/6-31G* level revealed the unexpected stability of this cis-cup-conformer of tris(DPAF-C9) better than that of the stereoisomer in a propeller-form and the trans-conformer. The structural geometry is proposed to be capable of minimizing the aggregation related self-quenching effect in the condensed phase. Fluorescence emission wavelength of tris(DPAF-C9) was found to be in a close range to that of PVK that led to its potential uses as the secondary blue hole-transporting material for enhancing the device property toward the modulation of PLED performance.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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