Self-Assembling and Luminescent Properties of Chiral Bisoxadiazole Derivatives in Solution and Liquid-Crystalline Phases.
Herein, we report the synthesis, self-assembly, and electroluminescence characteristics of a new green-emitting, pseudodiscoid chiral molecule, OXDC, containing an electron-donating stilbene core and an electron-accepting oxadiazole substituent. The helical organization and specific interaction of the chiral pseudodiscoid molecule resulted in the formation of self-assembled nanofibers with a columnar superstructure. Macroscopic chirality was observed in both the liquid-crystalline phases and the self-assembled nanofibers of OXDC, a feature which was absent in the analogous achiral oxadiazole derivative reported earlier [ Sivadas , A. P. ; Supergelation via Purely Aromatic π-π Driven Self-Assembly of Pseudodiscotic Oxadiazole Mesogens . J. Am. Chem. Soc. 2014 , 136 , 5416 - 5423 ]. A high-performance organic light-emitting device was demonstrated using OXDC as the emitting material, with a luminous intensity of 10 115 cd m-2at 5 V and chromaticity coordinates of (0.32, 0.51).
Photosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR-NIIST) and Network of Institutes for Solar Energy, CSIR , Trivandrum 695019, India.
Aneesh P
AP
Sivadas
Centre for Nano and Soft Matter Sciences , Jalahalli, Bangalore 560013, India.
D S Shankar
0000-0002-9643-6604
DS
Rao
Photosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR-NIIST) and Network of Institutes for Solar Energy, CSIR , Trivandrum 695019, India.
N S Saleesh
NS
Kumar
Photosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR-NIIST) and Network of Institutes for Solar Energy, CSIR , Trivandrum 695019, India.
Deepak D
DD
Prabhu
Photosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR-NIIST) and Network of Institutes for Solar Energy, CSIR , Trivandrum 695019, India.
Shinto
S
Varghese
Department of Chemistry, Indian Institute of Technology Roorkee , Roorkee, Uttarakhand 247667, India.
C N
0000-0003-2331-5374
CN
Ramachandran
Photosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR-NIIST) and Network of Institutes for Solar Energy, CSIR , Trivandrum 695019, India.|Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST , Trivandrum 695019, India.
Rahul M
RM
Ongungal
Centre for Nano and Soft Matter Sciences , Jalahalli, Bangalore 560013, India.
S
S
Krishna Prasad
Photosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR-NIIST) and Network of Institutes for Solar Energy, CSIR , Trivandrum 695019, India.|Kerala State Council for Science Technology and Environment , Sasthra Bhavan, Pattom, Trivandrum 695004, India.|Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST , Trivandrum 695019, India.
Suresh
0000-0002-8903-7285
S
Das