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Keywords:

  • fullerenes;
  • photophysics;
  • porphyrinoids;
  • shape amphiphiles

Abstract

Molecules constructed from a combination of zero-dimensional ([60]fullerene (C60)) and two-dimensional (porphyrin (Por)) nanobuilding blocks represent an intriguing category of sphere–square “shape amphiphiles”. These sphere–square shape amphiphiles possess interesting optoelectronic properties. To efficiently synthesize a large variety of C60–Por shape amphiphiles, a facile route based on Steglich esterification was developed. The synthetic strategy enables the preparation of hydroxy-functionalized Por precursors (9, 10, 11, 12) with high purity in a one-pot procedure. All of the C60–Por shape amphiphiles (1, 2, 3, 4, 5) can be readily synthesized in good yields through subsequent Steglich esterification with a highly soluble carboxylic acid derivative of methanofullerene (13). Photophysical studies indicated weak electronic coupling between the C60 and Por moieties and suggest an edge-to-face alignment for the moieties. The fluorescence of electronically excited Por portions of each amphiphile was efficiently quenched, which was indicative of electron transfer from 1Por to the C60 group(s). Increasing the number of C60 groups on the shape amphiphiles led to more pronounced quenching of the Por fluorescence, which indicated the potential for more effective generation of charge-separated species, C60−.Por+., from the photoexcited C60–Por shape amphiphiles.

Featured Compounds

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  1. 1 - 13
Compound 9
Molecular Weight:2649.9167
Molecular Formula:C173H258N4O16
InChIKey:ZURUWFYBDFWSGB-ZPAMKMRSSA-N
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Compound 10
Molecular Weight:1992.8557
Molecular Formula:C130H182N4O12
InChIKey:SRFPRLFFENWEQQ-NHFQNWIJSA-N
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Compound 11
Molecular Weight:1992.8557
Molecular Formula:C130H182N4O12
InChIKey:BFOSZQUXQSYDQX-NQRGKPSMSA-N
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Compound 12
Molecular Weight:1335.7946
Molecular Formula:C87H106N4O8
InChIKey:UMZGSEXLNAMNGB-BRAKNJGWSA-N
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Compound 1
Molecular Weight:3971.3845
Molecular Formula:C269H314N4O23
InChIKey:XMPBQORYXIGFKL-NKEBUTLCSA-N
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Compound 2
Molecular Weight:4635.791
Molecular Formula:C322H294N4O26
InChIKey:KUMITYKPCGSCAF-YRZMIYKVSA-N
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Compound 3
Molecular Weight:4635.791
Molecular Formula:C322H294N4O26
InChIKey:GAPIIROVGPCALW-QPQDGNGFSA-N
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Compound 4
Molecular Weight:5300.1973
Molecular Formula:C375H274N4O29
InChIKey:KEYAVULUIDHNCH-XZPNJMHUSA-N
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Compound 5
Molecular Weight:5964.604
Molecular Formula:C428H254N4O32
InChIKey:AITAWZFYLWHVHW-FJBVMPNZSA-N
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Compound 13
Molecular Weight:1339.4829
Molecular Formula:C96H58O8
InChIKey:GXSWEVOAVCWTLC-UHFFFAOYSA-N
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Compound 6
Molecular Weight:678.7334
Molecular Formula:C44H30N4O4
InChIKey:VFHDWGAEEDVVPD-LWQDQPMZSA-N
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Compound 7
Molecular Weight:675.0764
Molecular Formula:C43H78O5
InChIKey:CEJSFFKDFWPORO-UHFFFAOYSA-N
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Compound 8
Molecular Weight:3306.978
Molecular Formula:C216H334N4O20
InChIKey:MPTHUNKWGVZGEF-BOZTZBAISA-N
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