N-trityl-2'-[2-[9,10-bis(1,3-dithiol-2-ylidene)anthracenyl]]pyrrolidino[3',4':1,2][60]fullerene

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-trityl-2'-[2-[9,10-bis(1,3-dithiol-2-ylidene)anthracenyl]]pyrrolidino[3',4':1,2][60]fullerene
• 化学式: C₁₀₁H₂₉NS₄
• 分子量: 1384.61
• InChiKey: VWVVZZCLBKQATD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26
• 重原子数：
  106
• 可旋转键数：
  5
• 环数：
  41.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸 、 N-trityl-2'-[2-[9,10-bis(1,3-dithiol-2-ylidene)anthracenyl]]pyrrolidino[3',4':1,2][60]fullerene 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Donor/Acceptor Fulleropyrrolidine Triads

  摘要：

  New C-60-based triads, constituted by a fulleropyrrolidine moiety and two different electroactive units [donor I-donor 2 (10, 15a,b), or donor 1-acceptor (17, 21)], have been synthesized by 1,3-dipolar cycloaddition reaction of azomethyne ylides to C-60 and further acylation reaction on the pyrrolidine nitrogen. The electrochemical study reveals some electronic interaction between the redox-active chromophores. Triads bearing tetrathiafulvalene (TTF) and ferrocene (Fe) (10) or pi-extended TTFs and Fe (15a,b) show reduction potentials for the C-60 moiety which are cathodically shifted in comparison to the parent C-60 In contrast, triads endowed with Fe and anthraquinone (AQ) (17) or Fe and tetracyanoanthraquinodimethane (TCAQ) (21) present reduction potentials for the C-60 moiety similar to C-60 Fluorescence experiments and time-resolved transient absorption spectroscopy reveal intramolecular electron transfer (ET) processes from the stronger electron donor (i.e., TTF or extended TTF) to the fullerene singlet excited state, rather than from the poorer ferrocene donor in 10, 15a,b. No evidence for a subsequent ET from ferrocene to TTF.+ or pi-extended TTF.+ was observed.

  DOI：

  10.1021/jo0005767
• 作为产物：
  描述：

  N-(三苯甲基)甘氨酸 、 足球烯 、 2-formyl-9,10-bis(1,3-dithiol-2-ylidene)dihydroanthracene 以 various solvent(s) 为溶剂， 反应 2.0h， 以63%的产率得到N-trityl-2'-[2-[9,10-bis(1,3-dithiol-2-ylidene)anthracenyl]]pyrrolidino[3',4':1,2][60]fullerene
  参考文献：
  名称：

  Donor/Acceptor Fulleropyrrolidine Triads

  摘要：

  New C-60-based triads, constituted by a fulleropyrrolidine moiety and two different electroactive units [donor I-donor 2 (10, 15a,b), or donor 1-acceptor (17, 21)], have been synthesized by 1,3-dipolar cycloaddition reaction of azomethyne ylides to C-60 and further acylation reaction on the pyrrolidine nitrogen. The electrochemical study reveals some electronic interaction between the redox-active chromophores. Triads bearing tetrathiafulvalene (TTF) and ferrocene (Fe) (10) or pi-extended TTFs and Fe (15a,b) show reduction potentials for the C-60 moiety which are cathodically shifted in comparison to the parent C-60 In contrast, triads endowed with Fe and anthraquinone (AQ) (17) or Fe and tetracyanoanthraquinodimethane (TCAQ) (21) present reduction potentials for the C-60 moiety similar to C-60 Fluorescence experiments and time-resolved transient absorption spectroscopy reveal intramolecular electron transfer (ET) processes from the stronger electron donor (i.e., TTF or extended TTF) to the fullerene singlet excited state, rather than from the poorer ferrocene donor in 10, 15a,b. No evidence for a subsequent ET from ferrocene to TTF.+ or pi-extended TTF.+ was observed.

  DOI：

  10.1021/jo0005767

文献信息

• Donor/Acceptor Fulleropyrrolidine Triads
  作者：M. Ángeles Herranz、Beatriz Illescas、Nazario Martín、Chuping Luo、Dirk M. Guldi

  DOI：10.1021/jo0005767

  日期：2000.9.1

  New C-60-based triads, constituted by a fulleropyrrolidine moiety and two different electroactive units [donor I-donor 2 (10, 15a,b), or donor 1-acceptor (17, 21)], have been synthesized by 1,3-dipolar cycloaddition reaction of azomethyne ylides to C-60 and further acylation reaction on the pyrrolidine nitrogen. The electrochemical study reveals some electronic interaction between the redox-active chromophores. Triads bearing tetrathiafulvalene (TTF) and ferrocene (Fe) (10) or pi-extended TTFs and Fe (15a,b) show reduction potentials for the C-60 moiety which are cathodically shifted in comparison to the parent C-60 In contrast, triads endowed with Fe and anthraquinone (AQ) (17) or Fe and tetracyanoanthraquinodimethane (TCAQ) (21) present reduction potentials for the C-60 moiety similar to C-60 Fluorescence experiments and time-resolved transient absorption spectroscopy reveal intramolecular electron transfer (ET) processes from the stronger electron donor (i.e., TTF or extended TTF) to the fullerene singlet excited state, rather than from the poorer ferrocene donor in 10, 15a,b. No evidence for a subsequent ET from ferrocene to TTF.+ or pi-extended TTF.+ was observed.