Chemical Science of π-Electron Systems by Takeshi Akasaka, Atsuhiro Osuka, Shunichi Fukuzumi, Hideki

By Takeshi Akasaka, Atsuhiro Osuka, Shunichi Fukuzumi, Hideki Kandori, Yoshio Aso

This booklet offers the main complicated evaluation to be had of all facets of π-electron structures, together with novel constructions, new man made protocols, chemical and actual houses, spectroscopic and computational insights, molecular engineering, equipment homes and physiological houses. π-Electron platforms are ubiquitous in nature. vegetation convert gentle power into chemical power via photosynthetic tactics, within which chlorophylls and different porphyrinoids play a big position. at the one hand, learn to profit approximately photosynthesis from nature has ended in knowing of electron and effort move tactics and to attaining synthetic power conversion platforms encouraged by way of nature. nevertheless, fresh advances in natural and inorganic chemistry give the opportunity to build novel π-electron structures that had by no means existed in nature. The authors of this e-book are from various examine fields together with natural chemistry, inorganic chemistry, actual chemistry, fabrics technological know-how, and biology, offering a entire assessment of π-electron platforms for a large readership. not just experts but additionally graduate scholars operating in π-electron structures will locate the booklet of significant curiosity. all through, the various capability for destiny fruitful purposes of π-electron platforms is printed to the reader.

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Naphthal-1,5-diyne generated by treatment of 43 with KF with the aid of 18-crown-6 reacted with 1,3-cyclohexadiene to give diethanochrysene 44 in a low yield. In spite of all of our efforts, the yield could not be improved. This low yield was attributed to the intrinsic low reactivity of 1,3-cyclohexadiene, 28 H. Uno et al. ), AcOH, 80 ı C; TMSCl, pyridine, toluene; n BuLi, TMSCl, THF; n BuLi, Tf2 O, THF, ether; (ii) 1,3-cyclohexadiene, KF, 18-crown6; (iii) PhSCl, CH2 Cl2 , 0 ı C; mCPBA, CH2 Cl2 , 0 ı C; DBU, CH2 Cl2 , rt; DDQ, dioxane, rt; CNCH2 CO2 Et, KOt Bu, THF, rt; (iv) KOH, ethylene glycol, 170–190 ı C; (v) 8a, TFA, CH2 Cl2 , 50 ı C; Et3 N, DDQ, CH2 Cl2 ; Zn(OAc)2 2H2 O; (vi) 200 ı C, in vacuo because the naphthaldiyne had smoothly reacted with 1,3-cyclopentadiene to give the corresponding dimethanochrysene in a good yield.

1007/978-4-431-55357-1_3 37 38 M. Akiyama et al. The helical topology of helicenes provides high optical rotations, high circular dichroism values, and several enhanced physical organic properties. This is especially true if supramolecular chirality is generated from a self-assembly of helicenes. Here in this chapter, examples of higher-order molecular architectures of helicenes and their related compounds in aggregates, in crystals, and in macromolecules connected by covalent bonds will be summarized.

Most recently, Hasobe et al. reported the synthesis of quinoxaline-fused [7]carbohelicene 10 (Fig. 9) [14]. In crystal state, P-enantiomer of 10 formed dimers, while 42 M. Akiyama et al. EtO2C EtO2C S N R N R S 9a: R = Cl 9b: R = SMe Fig. 8 Crystal packing of racemic and enantiopure helicene 9a (Reprinted with permission from Ref. [13]. Copyright 2013, Wiley-VCH Verlag GmbH & Co. 7 A CH x interaction Fig. 9 Homochiral dimer of P-10 and helical columnar stack from racemic 10 [(a) Packing mode along the b axis; (b) Packing mode along the a axis; and (c) -stacking between two neighboring P-10 with intermolecular distance.

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