With hydrogen to control the electronic and molecular structure of ultra-conjugated molecules

Control conjugated system organic supramolecular structure For the performance of the organic transistors, and organic solar cells have a decisive influence, but their precise assembly remains an unsolved challenge. Halogen bonds, hydrogen bonds, etc. in recent years as a method of supramolecular received a lot of attention in the field of conjugate, but they generally lack direction, also ignores the impact of possible electronic structure. Recently, after 00 McGill University professor Dmitrii Perepichka Study Group PhD Liucheng Hao as the first author reported a both can be precisely controlled supramolecular structure conjugated system, and can be controllably varied significantly donor – acceptor electronic structure . The work titled \”Extraordinary Enhancement of π-Electron Donor / Acceptor Ability by DD / AA Complementary Hydrogen Bonding\” published in the top journals in chemistry Angewandte Chemie. 用氢键来控制共轭分子的电子和超分子结构 using the DD / AA two-dot complementary hydrogen bonds, of a series of assembled oriented indole and carbazole, and o-benzoquinone conjugated eutectic. Hydrogen induced polarization success of these weak donor – acceptor become strong donor – acceptor, such that the highest band gap energy is reduced 1.5 eV (Experimental band gap energy of 1.59-0.65 eV).

用氢键来控制共轭分子的电子和超分子结构
FIG. (A) B3LYP / 6-31G (d) orbital energy calculation. Donor (indole and carbazole) highest occupied molecular orbital (HOMO) and acceptor (o-benzoquinone) the lowest unoccupied molecular orbital (LUMO) is black, the HOMO and HOMO blue marked changes, changes LUMO and LUMO marked in red. Labeled binding energy at the bottom of FIG. The principle of changing (b) the electronic structure of FIG.
用氢键来控制共轭分子的电子和超分子结构
FIG. X-ray diffraction analysis of the resulting eutectic structure comprising eutectic front and side view, pi-stacking structure (donor blue, red for the receptor) and the corresponding spacing Super (d∥).

This controlled electronic structure changes directly reflected in the performance of the semiconductor preparation of – charge transport speed is several orders of magnitude improvement, and respectively, p-type regulation, bipolar, the present intrinsic semiconductor.

用氢键来控制共轭分子的电子和超分子结构
FIG. IC-AceNap (a, p- type), IC-Diaza (b, intrinsic), IC-PyT (c, bipolar) data organic field effect transistor.

The authors also carried out a series of electrochemical, electronic spectra and vibration spectrum, electron spin resonance (the ESR), phototransistors study to clarify the relationship between the structural characteristics of this new charge transfer complex. This work is expected to play an important role in morphology (intrinsic) semiconductor design and the electronic regulation of the solar cell structure. As used herein a subject in a first degree of Liucheng Hao graduation (2016 undergraduate) designed, carried out except that the transistor design, synthesis, assembly, characterization work. The full text link: https: //onlinelibrary_wiley.gg363.site/doi/abs/10.1002/ange.201910288

相关新闻