Synthesis And Properties Of Imide Derivatives Based On The Three-dimensional Structure Of Trinaphthalene[3,3,3]spiralan

Three-dimensional(3D)materials have developed rapidly in recent years,but they are mainly concentrated on molecules that form curved surfaces through twisting and bending.However,the three-dimensional rigid organic conjugated molecules with symmetrical structure develop slowly because of the lack of alternative parent units and the complex chemical reaction process.Among them,trinaphthyl[3,3,3]spiroplasmane(TNP),as a compound with a rigid structure of D3h symmetry,has a larger free cavity in the molecule and more reaction sites,which has attracted people's attention.However,a larger ? plane will increase the intermolecular force and decrease the solubility.Therefore,the introduction of imide groups can not only increase the solubility,but also reduce the LUMO energy level to improve the stability of the molecules.The research work of this thesis is to select trinaphthalene[3,3,3]spiroplasmane as the functional skeleton,design and synthesize three-dimensional symmetrical fused ring aromatic imide compounds containing naphthalene and perylene structures,that is,a new type of imide-containing compound Amine organic conjugated functional molecules.The photoelectric properties of trinaphthyl monoimide[3,3,3]spiroplasmane were studied,and the performance of the device was preliminary explored by using it as the blue light-emitting layer in organic light-emitting diodes(OLED).The main research contents are as follows:1.Through multiple and efficient selective bromination and esterification of trinaphthyl[3,3,3]spirolane to obtain hexa-esterified derivatives,then hydrolysis dehydration and amidation to obtain trinaphthyl monoacyls containing different alkyl chains Imine[3,3,3]spiroplasmane.Its optical and electrical properties also indicate that there is homo-conjugation effect in this three-dimensional molecule.Different alkyl chain substituents will affect the crystal packing form,and the packing of fluorine-containing alkyl chains is hexagonal honeycomb.The fluorine-containing alkyl chain material is used as the light-emitting layer of the OLED,which emits blue light at 409 nm,and its brightness reaches 2944 cd m-2,showing its excellent performance as a blue light-emitting compound.2.Through the selective bromination,coupling and dehydrocyclization of trinaphthalene[3,3,3]spiralan,a new three-dimensional framework molecule with a larger intramolecular free cavity with a perylene structure in the middle of the naphthalene unit is obtained.And the target compound 4NMIDT-C8 with good solubility can be obtained by the tribromation of trinaphthyl[3,3,3]spirosylane,selective coupling reaction,further hydrolysis,dehydration and amidation reaction.The maximum absorption wavelength and the maximum molar extinction coefficient of the UV absorption spectrum will change greatly after unconjugated and theoretically fully conjugated,and its fully conjugated frontier orbit is calculated through theoretical calculations,and its 1/2 structure In comparison,although the energy level of LUMO does not change much,its HOMO is more distributed in the middle perylene unit,and in comparison,it has a larger cavity and a larger ?-conjugated plane in the molecule,which is found in organic eutectic Certain research value and can be cultivated in eutectic with some organic acceptor molecules.