950839-30-2

Basic information

• Product Name: 2-(4-(9H-carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole
• Synonyms: 2-(4-(9H-carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole
• CAS NO: 950839-30-2
• Molecular Weight: 387.44
• Mol File: 950839-30-2.mol

Chemical Properties

• CAS DataBase Reference: 2-(4-(9H-carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-(9H-carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole(950839-30-2)
• EPA Substance Registry System: 2-(4-(9H-carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole(950839-30-2)

Safety Data

• Hazardous Substances Data: 950839-30-2(Hazardous Substances Data)

Upstream product

• 57103-17-0 N-(4-cyanophenyl)carbazole 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 642097-34-5 9-(4-(1H-tetrazol-5-yl)phenyl)-9H-carbazole 
• 98-88-4 benzoyl chloride 
• 21510-43-0 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole 
• 86-74-8 9H-carbazole 
• 6781-60-8 N′-benzoyl-4-bromobenzohydrazide 
• 5933-32-4 4-bromobenzoic acid hydrazide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 50907-21-6 5-(4-fluorophenyl)-1H-1,2,3,4-tetrazole 
• 1194-02-1 4-fluorobenzonitrile 
• 1580-50-3 2-(4-fluorophenyl)-5-phenyl-1,3,4-oxadiazole 

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This article sheds new light on the interplay of electronic and conformational effects in luminescent bipolar molecules. A series of carbazole/1,3,4-oxadiazole hybrid molecules is described in which the optoelectronic properties are systematically varied by substituent effects which tune the intramolecular torsion angles. The synthesis, photophysical properties, cyclic voltammetric data, X-ray crystal structures, and DFT calculations are presented. Excited state intramolecular charge transfer (ICT) is observed from the donor carbazole/2,7-dimethoxycarbazole to the acceptor phenyl/diphenyloxadiazole moieties. Introducing more bulky substituents onto the diphenyloxadiazole fragment systematically increases the singlet and triplet energy levels (ES and ET) and blue shifts the absorption and emission bands. The triplet excited state is located mostly on the oxadiazole unit. The introduction of 2,7-dimethoxy substituents onto the carbazole moiety lowers the value of ES, although ET is unaffected, which means that the singlet-triplet gap is reduced (for 7bE S - ET = 0.61 eV). A strategy has been established for achieving unusually high triplet levels for bipolar molecules (ET = 2.64-2.78 eV at 14 K) while at the same time limiting the increase in the singlet energy.