Heavy atom induced phosphorescence of organic materials using mono- and trifunctional organomercury derivatives

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Title: Heavy atom induced phosphorescence of organic materials using mono- and trifunctional organomercury derivatives
Author: Burress, Charlotte Nicole
Abstract: This dissertation focuses on the phosphorescence of organic chromophores using perfluoro -ortho -phenylene mercury (1 ) and bis (pentafluorophenyl )mercury (2 ) as external heavy atom effect inducers . To ascertain the suitability of these luminescent adducts for OLED applications , several research objectives have been investigated . To further shorten the triplet lifetimes of adducts involving 1 , a strategy was developed which combines both internal and external heavy atom effects . Specifically , complexes involving 1 and N -methylcarbazole , N -methylindole and the 1 - halonaphthalenes were investigated . The existence and stability of the complexes could be confirmed in solution by fluorescence spectroscopy . In the solid state , these adducts form supramolecular binary stacks where the molecules of 1 alternate with the aromatic substrate . As a result of the mercury external heavy atom effect , all of these adducts display intense room temperature phosphorescence of the free arene . With the Nheterocycles , the triplet lifetimes were drastically reduced to below 100 mu -s . To appreciate the origin of the unusual heavy atom effects observed in arene adducts with 1 , 2 was studied as a monofunctional analog to 1 . By utilizing fluorescence spectroscopy , naphthalene , biphenyl , and fluorene complexes of 1 and 2 have been detected in solution . The solid state structure of the adducts with 2 reveal supramolecular binary stacks . Comparison of the photophysical results supports the occurrence of cooperative effects between the Lewis acidic mercury centers of 1 , which make it a more efficient external heavy -atom effect inducer . Polymeric materials which are amenable to deposition in thin layers were investigated as substrates for 1 and 2 . Both poly (vinyl -2 -naphthalene ) and poly (vinylcarbazole ) interact with 1 and 2 in solution as evidenced by fluorescence spectroscopy . With the solid blend 1 ?PVK , a small doping percentage of 1 results in white emission , while larger percentages of 1 yield bright orange emission . This dissertation presents the first structurally characterized ternary complex with 1 , carbazole , and coordinating solvents THF and triethylamine . IR spectroscopy and short N ? ? ?O and N ? ? ?N distances in the solid state indicates that the acidic N -H moiety of carbazole interacts with the solvent by hydrogen bonding . In the extended structure , molecules of 1 and the hydrogen bonded complex alternate to form supramolecules .
URI: http : / /hdl .handle .net /1969 .1 /ETD -TAMU -1052
Date: 2009-05-15

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Heavy atom induced phosphorescence of organic materials using mono- and trifunctional organomercury derivatives. Available electronically from http : / /hdl .handle .net /1969 .1 /ETD -TAMU -1052 .

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