Next Article in Journal
Potential Role of Olive Oil Phenolic Compounds in the Prevention of Neurodegenerative Diseases
Next Article in Special Issue
Light-Induced Infrared Difference Spectroscopy in the Investigation of Light Harvesting Complexes
Previous Article in Journal
Construction of an Isonucleoside on a 2,6-Dioxobicyclo[3.2.0]-heptane Skeleton
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(3), 4635-4654; doi:10.3390/molecules20034635

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

1
Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts Lowell, Lowell, MA 01854, USA
2
Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
3
Advanced Photonics Research Institute, Gwangju Institute of Science and Technology, Gwangju 500–712, Korea
4
AFRL/RXBN, Air Force Research Laboratory, Wright-Patterson Air Force Base, Dayton, OH 45433, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Pall Thordarson
Received: 12 January 2015 / Revised: 4 March 2015 / Accepted: 4 March 2015 / Published: 13 March 2015
(This article belongs to the Special Issue Light-Harvesting Complexes)
View Full-Text   |   Download PDF [3111 KB, uploaded 13 March 2015]   |  

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. View Full-Text
Keywords: cis-tris(diphenylaminofluorene); light-harvesting nanostructure; light emitting chromophore; geometrically hindered diphenylaminofluorene; nonplanar stereoisomer cis-tris(diphenylaminofluorene); light-harvesting nanostructure; light emitting chromophore; geometrically hindered diphenylaminofluorene; nonplanar stereoisomer
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Kang, N.-G.; Kokubo, K.; Jeon, S.; Wang, M.; Lee, C.-L.; Canteenwala, T.; Tan, L.-S.; Chiang, L.Y. Synthesis and Photoluminescent Properties of Geometrically Hindered cis-Tris(diphenylaminofluorene) as Precursors to Light-Emitting Devices. Molecules 2015, 20, 4635-4654.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top