Comparative study of spectroscopic properties of α- or β-butyloxy-substituted tribenzotetraazachlorin-fullerene conjugates

被引：4
|
作者：
Fukuda, Takamitsu [1 ]
Kaneko, Hironori [1 ]
Kobayashi, Nagao [1 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
来源：
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES | 2009年 / 13卷 / 10期
基金：
日本学术振兴会;
关键词：
chlorin; phthalocyanine; fullerene; PHOTOINDUCED ELECTRON-TRANSFER; ZINC NAPHTHALOCYANINES; METAL-FREE; PHTHALOCYANINE; TETRAAZACHLORINS; ABSORPTION; SEPARATION; STATES; DYES; DYAD;
D O I：
10.1142/S1088424609001327
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Mixed condensation of 1,2-dicyanofullerene (1) and 3,6-dibutyloxyphthalonitrile (2a) in the presence of nickel chloride dihydrate (NiCl2 center dot 2H(2)O) in quinoline forms an alpha-hexabutyloxy-substituted tribenzotetraazachlorin (TBTAC)-fullerene (C-60) conjugate (3). UV-vis absorption and magnetic circular dichroism (MCD) properties of 3 have been obtained, and the results compared with those of the beta-substituted isomer (4). Although the absorption spectra of 3 and 4 are similar in shape, a significant band shift to longer wavelength is observed for 3. According to the results of DFT calculations, the observed spectroscopic differences are ascribed to differences in the distribution of the MO amplitudes at the alpha- and beta-positions of the TBTAC moiety.
引用
收藏
页码：999 / 1005
页数：7
相关论文
共 50 条
  • [1] Metal effects on electronic structures of directly linked tribenzotetraazachlorin-fullerene conjugates
    Fukuda, Takamitsu
    Masuda, Satoshi
    Hashimoto, Naoaki
    Kobayashi, Nagao
    INORGANIC CHEMISTRY, 2008, 47 (07) : 2576 - 2580
  • [2] Reduction-triggered aromatic to aromatic electronic structure switching in tribenzotetraazachlorin-fullerene conjugates
    Fukuda, Takamitsu
    Sato, Jun
    Hashimoto, Naoaki
    Kobayashi, Nagao
    CHEMICAL COMMUNICATIONS, 2014, 50 (91) : 14269 - 14272
  • [3] Metal (Co, Fe) tribenzotetraazachlorin-fullerene conjugates: Impact of direct π-bonding on the redox behaviour and oxygen reduction reaction
    Ozoemena, Kenneth I.
    Mamuru, Solomon A.
    Fukuda, Takamitsu
    Kobayashi, Nagao
    Nyokong, Tebello
    ELECTROCHEMISTRY COMMUNICATIONS, 2009, 11 (06) : 1221 - 1225
  • [4] Electroabsorption spectra of directly linked tribenzotetraazachlorin-fullerene conjugates having either electron donating or withdrawing substituents in a polymer film
    Fukuda, Takamitsu
    Masuda, Satoshi
    Wahadoszamen, Md.
    Ohta, Nobuhiro
    Kobayashi, Nagao
    DALTON TRANSACTIONS, 2009, (31) : 6089 - 6091
  • [5] Synthesis and electronic properties of fullerene derivatives substituted with oligophenylenevinylen-ferrocene conjugates
    Figueira-Duarte, Teresa M.
    Rio, Yannick
    Listorti, Andrea
    Delavaux-Nicot, Beatrice
    Holler, Michel
    Marchioni, Filippo
    Ceroni, Paola
    Armaroli, Nicola
    Nierengarten, Jean-Francois
    NEW JOURNAL OF CHEMISTRY, 2008, 32 (01) : 54 - 64
  • [6] A Comparative Study of Electrochemical, Spectroscopic and Structural Properties of Phenyl, Thienyl and Furyl Substituted Ethylenes
    Viglianti, Lucia
    Villafiorita-Monteleone, Francesca
    Botta, Chiara
    Mussini, Patrizia R.
    Ortoleva, Emanuele
    Cauteruccio, Silvia
    Licandro, Emanuela
    Baldoli, Clara
    CHEMISTRYSELECT, 2017, 2 (09): : 2763 - 2773
  • [7] Synthesis and Spectroscopic Properties of Covalent Albumin Conjugates of Phthalocyanine Zincs Substituted with Metadicarboxyphenoxyl Groups
    Xiao Rong-ping
    Huang Jian-dong
    Zhang Han-hui
    SPECTROSCOPY AND SPECTRAL ANALYSIS, 2011, 31 (05) : 1322 - 1327
  • [8] Synthesis and Spectroscopic Properties of Phthalocyanine-[60]Fullerene Conjugates Connected Directly by Means of a Four-Membered Ring
    Fukuda, Takamitsu
    Kikukawa, Yuu
    Takaishi, Shiori
    Kobayashi, Nagao
    CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (04) : 751 - 758
  • [9] Synthesis of regioisomerically pure piperidine substituted perylenebisimide NIR dyes: A comparative study of spectroscopic, electrochemical and crystalline properties
    Hussain, Ejaz
    Zhou, Huipeng
    Yang, Na
    Shahzad, Sohail Anjum
    Yu, Cong
    DYES AND PIGMENTS, 2017, 147 : 211 - 224
  • [10] Systematic study of the spectroscopic properties of isotopically substituted water by MD simulations
    Lu, TH
    Toth, G
    Heinzinger, K
    JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (04): : 1336 - 1339
12345