Degutytė, Rimgailė

The synthesis by Suzuki cross-coupling and properties of a glass-forming star-shaped compound tris(9-(3-methylphenyl)carbazol-3-yl)-triphenylamine are reported. The thermal, optical, photoelectrical andelectrochemical properties of the hole-transporting compound were studied by differencial scanningcalorimetry, thermogravimetric analysis, UV/vis spectroscopy, electron photoemission, time-of-flighttechnique and cyclic voltammetry. The compound exhibits high thermal stability with a the temper-ature of the onset of the thermal degradation of 510◦C. The compound absorbs in 200–400 nm rangeand possesses an optical band gap of 3.15 eV, avoiding any screening effect with the dye. The solid stateionization potential (IPss) of the molecule, measured by electron photoemission and cyclic voltammetryis around 5 eV similar to the standard spiroOMeTAD hole-transporting material. The hole drift mobil-ity in the amorphous layer of reported compound reach 6.4 × 10−5cm2/Vs under high electrical field(6.4 × 105V/cm). This synthesized derivative was finally assessed as hole transporting material in thesolid state dye-senstized solar cells with (5-(1,2,3,3a,4,8b-hexahydro-4-[4-(2,2-diphenylvinyl)phenyl]-cyclopeanta[b]indole-7-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-yl)acetic acid (D102) as sensitizerand showed a power conversion efficiency of 0.63% under standard solar irradiation (100 mW/cm2,AM1.5).

The field of organic electro-optic and electronic devices is in constant development. Organic semiconductors are used in devices like OLEDs (organic light-emitting diodes), solar cells, field – effect transistors and offer potential for low cost fabrication, ease of processing, and possibility of flexible device manufacture. Among wide of organic demiconductors usually possessing large conjugated π electron systems, there are some noteworthy small-system exceptions [1] demonstrating semiconducting properties (especially charge mobility) rivalling those of counterpart compounds containing large π conjugated systems. These compounds have the planes of their small π systems oriented in an angle-fashion bestowing the coupling between them. Tröger's base is V-shaped C₂-symmetric chiral molecule consisting of a bicyclic aliphatic methanodiazocine unit fused with two aromatic rings. Its structure allows it to be used as a core and provide angle orientation for the conjugated π systems attached to it and therefore potentially create coupling between them. Some recent research have shown that besides connecting aromatic fragments only geometrically the non-conjugated bridge in Tröger's base can also bestow electronic connecting in the absence of a π linker [2]. These findings prompt interest for synthesis and research of the new potential Tröger's base core containing semiconducting compounds [...].

N,N-Di(3-chloro-2-hydroxypropyl)-N,N-di(9-ethyl-9H-carbazolyl)-2,7-diaminonaphthalene upon intramolecular cyclization gives 1,8-bis(9-ethyl-9H-carbazol-3-yl)-1,2,3,4,5,6,7,8- octahydroquino[5,6-f]quinoline-3,6-diol.

KTU Organinės chemijos katedroje, tiriant aromatinių aminų sąveiką su epichlorhidrinu, buvo susintetinti įvairūs monofunkciniai ir bifunkciniai 1,2,3,4-tetrahidrochinolino dariniai [1-5]. Šio darbo tikslas buvo ištirti N,N-(9-etil-9H-karbazol-3-il)-2,7-diaminonaftaleno sąveiką su epichlorhidrinu, tikslu gauti junginį, turintį du 1,2,3,4-tetrahidrochinolino žiedus. N,N-(9-etil-9H-karbazol-3-il)-2,7-diaminonaftalenas buvo gautas 1 ir 2 kondensacijos reakcijos metu, dalyvaujant katalizatoriui I2. Epoksidarinio 5 nepavykus gauti, alkilinant diaminą 3 epichlorhidrinu, reakcijoje dalyvaujant KOH, buvo pasirinktos kitos sintezės sąlygos. [...].

N,N-di(3-chloro-2-hydroxypropyl)-N,N-di(2-naphthyl)-1,4-diaminobenzene upon intra- molecular cyclization gives bis-1,2,3,4-tetrahydroquinoline derivative - 4,4`-(1,4-phenylene)di(1,2,3,4-tetrahydrobenzo[f]quinolin-2-ol).

Tetrahydroquinolines are important functional moiety in a wide range of biologically active molecules. Also, some of them have found application in modern recording technologies. It is known, that 3-hydroxy-1-phenyl-1,2,3,4-tetrahydroquinoline can be prepared when diphenylamine is heated with epichlorohydrin via the intermediate n-(3-chloro-2-hydroxypropyl)diphenylamine. [...].

The synthesis of 4,4'-(1,4phenylene)-bis(2-hydroxy-1,2,3,4-tetrahydrobenzo[ƒ]quinoline) was performed by cyclization of N,N'-di(3-chloro-2-hydroxypropyl)-N,N'-di(2-naphtyl)-1,4-diaminobenzene.