Expanded π-electron systems, tri(phenanthro)hexaazatriphenylenes and tri(phenanthrolino)hexaazatriphenylenes, that are self-assembled to form one-dimensional aggregates

Journal of Organic Chemistry

Volumn 75, Issue 20, 2010, Pages 6858-6868

  Ishi I, Tsutomu ^a,b   Hirashima, Ryoichi ^a   Tsutsumi, Naotaka ^a   Amemori, Shogo ^a   Matsuki, Shigeki ^a   Teshima, Yuuki ^a   Kuwahara, Rempei ^b   Mataka, Shuntaro ^b  

^a KURUME NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATE SPECIES; AROMATIC MOIETIES; CONCENTRATION DEPENDENCE; ELECTRON SYSTEMS; ELECTRON-DEFICIENT; FILM STATE; FLUORESCENCE QUANTUM YIELD; H NMR SPECTRA; HETEROAROMATICS; MALDI-TOF; MASS SPECTRA; NON-POLAR; PHENANTHROLINES; POLAR SOLVENTS; REDUCTION POTENTIAL; SELF-ASSEMBLED; SELF-ASSEMBLING; STACKING MODES; TETRAMERS; UV-VIS AND FLUORESCENCE SPECTRA; VOLTAMMETRY MEASUREMENTS;

AGGREGATES; CESIUM; CONDENSATION REACTIONS; CYCLIC VOLTAMMETRY; DICHLOROMETHANE; ELECTRONS; FLUORESCENCE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM YIELD;

ELECTRON AFFINITY;

ALKENE DERIVATIVE; ANILINE DERIVATIVE; DICHLOROMETHANE; HETEROCYCLIC COMPOUND; PHENANTHRENE; PHENANTHROLINE; PHENANTHROLINE DERIVATIVE; QUINONE DERIVATIVE; SOLVENT;

ARTICLE; CONCENTRATION RESPONSE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; FLUORESCENCE SPECTROSCOPY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REDUCTION; SEMICONDUCTOR; ULTRAVIOLET SPECTROSCOPY;

AZA COMPOUNDS; CHRYSENES; ELECTROCHEMISTRY; ELECTRONS; MICROSCOPY, ATOMIC FORCE; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 77957903557     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101212d     Document Type: Article

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77. The π-stacked one-dimensional aggregate is also supported by X-ray diffraction patterns of 6a, 6b, 6c, and 14b (Supporting Information). A weak reflection around 26° would be attributed to the intracolumnar π-stacking distance of ca. 0.34 nm. In contrast, a strongly sharp reflection around 2.9-3.7° (2.38 nm for 6a, 2.69 nm for 6b, 3.03 nm for 6c, and 2.85 nm for 14b) would be due to the intercolumnar packing.