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

Synthesis and photoluminescent properties of geometrically hindered cis-tris(diphenylaminofluorene) as precursors to light-emitting devices

Molecules. 2015 Mar 13;20(3):4635-54. doi: 10.3390/molecules20034635.

Authors

Nam-Goo Kang¹, Ken Kokubo², Seaho Jeon³, Min Wang⁴, Chang-Lyoul Lee⁵, Taizoon Canteenwala⁶, Loon-Seng Tan⁷, Long Y Chiang⁸

Affiliations

¹ Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA. papyrus92@gmail.com.
² Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. kokubo@chem.eng.osaka-u.ac.jp.
³ Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA. seaho_jeon@uml.edu.
⁴ Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA. wangmin81@gmail.com.
⁵ Advanced Photonics Research Institute, Gwangju Institute of Science and Technology, Gwangju 500-712, Korea. vsepr@gist.ac.kr.
⁶ Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA. taizoonc@hotmail.com.
⁷ AFRL/RXBN, Air Force Research Laboratory, Wright-Patterson Air Force Base, Dayton, OH 45433, USA. Loon-Seng.Tan@wpafb.af.mil.
⁸ Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA. Long_Chiang@uml.edu.

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Acetamides / chemical synthesis*
Acetamides / chemistry
Luminescent Agents / chemical synthesis*
Luminescent Agents / chemistry
Molecular Conformation
Spectrophotometry
Stereoisomerism

Substances

Acetamides
Luminescent Agents