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Based On The Synthesis And Properties Of The The Heteroatom Triangle Allyl Carbazole Organic Functional Materials

Posted on:2010-02-22Degree:DoctorType:Dissertation
Country:ChinaCandidate:H Q ZhangFull Text:PDF
GTID:1111360302457715Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
In this dissertation, two star shaped donor-acceptor dendrimers based on heterotriangulene and carbazole were synthesized through Ullmann reactions. The dendrimers show distinct ground state intramolecular charge transfer (ICT) transitions as confirmed by UV-vis along with cyclic voltammetric studies. The dendrimers show efficient aggregation-induced emissions originated from the carbazole dendrons, heterotriangulene core, intramolecular charge transfer (ICT) and intermolecular aggregation absorptions. The OLEDs fabricated with G1 and G2 as non-doping emitters exhibit exclusive aggregation-induced luminescence peaking at 600 and 630 nm, respectively, and demonstrate a good performance with maximum luminance of 1586 cd m-2 at current efficiency of 5.3 cd A-1 for G1 and 827 cd m-2 at current efficiency of 6.9 cd A-1 for G2.The largeπ-conjugation disc-like structure of heterotriangulene makes itself a good electron-attractive building block for star shaped electronic networks with potential applications for discotic liquid crystals and supramolecular assembly based electronic devices. Herein, we synthesized a series of disc like molecules incorporating heterotriangulene as rigid core, p-alkoxy phenylacetylene as side chains. The compounds with six to twelve side chains have good self-assembly properties, and the compounds with ten and twelve carbon side chains have column liquid crystal properties as well.A series of linear molecules with donor-acceptor-donor type, incorparating carbazole as donor, anthracene or benzothiadiazole as acceptor, have been synthesized. Different energy levels and band gaps of these molecules were tuned by adjusting the affinity of acceptors and effect conjugation length of theπbridges. The results of absorption, emission spectra and electrochemical studies indicate that the band gaps of these molecules are effectively controlled. Theoretical calculations were also conducted to gain further insight into the mechanisms, and gave good agreement with experiment. A new two nitrogen containing hetero-phenalenyl radical has been synthesized. The ESR spectra indicate that the radical is very stable. So, we are likely to synthesize six nitrogen containing hetero-phenalenyl radical, which is expected to show more stability. But to our surprise, the calculation results indicate that the homolytic bond dissociation enthalpy (BDE) of N-H bond for the precursor of six nitrogen containing hetero-phenalenyl radical is as high as 100 kcal mol-1, which overhead the ability of the oxidants such as silver oxide, active lead dioxide and S2Cl2 to abstract the hydrogen from the N-H bond.It is reported before that tetracene is good FET materials with high charge mobilites. But it has less stability. A proper modification to the tetracene is helpful to enhance the stability. Considering the stabilization of chlorine atom to electrons, we syntheszied 5,6,11,12-tetrachlorotetracene. Single crystal field-effect transistors based on tetrachlorotetracene were fabricated and showed p-type behaviors with the highest field-effect mobility of 1.7 cm2/V s.
Keywords/Search Tags:heterotriangulene, carbazole, organic light emitting diodes (OLED), self-assembly
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