Skip to main content

2020 | OriginalPaper | Buchkapitel

5. The Template-Directed Synthesis of a Fully Conjugated 14-Porphyrin Nanoball

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

The preparation of conjugated organic systems with strong π-orbital overlap between the molecular components is both challenging and laborious. This chapter describes the template-directed synthesis and characterisation of a π-conjugated 14-porphyrin nanoball. The bicyclic structure consists of a 6- and 10-porphyrin nanoring intersecting at two points. UV-Vis-NIR titrations were performed to investigate the binding behaviour of the templates inside the cavity of the ball. In addition, photoluminescence (PL) upconversion spectroscopy revealed strong coupling between the two rings. By removing the templates, the flexibility in the system increases which results in a decrease in the PL anisotropy. This indicates that excitations may migrate between the two ring components of the nanoball.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Richert S, Cremers J, Kuprov I, Peeks MD, Anderson HL, Timmel CR (2017) Constructive quantum interference in a bis-copper six-porphyrin nanoring. Nat Commun 8:14842CrossRefPubMedPubMedCentral Richert S, Cremers J, Kuprov I, Peeks MD, Anderson HL, Timmel CR (2017) Constructive quantum interference in a bis-copper six-porphyrin nanoring. Nat Commun 8:14842CrossRefPubMedPubMedCentral
2.
Zurück zum Zitat Peeks MD, Claridge TDW, Anderson HL (2017) Aromatic and antiaromatic ring currents in a molecular nanoring. Nature 541:200CrossRefPubMed Peeks MD, Claridge TDW, Anderson HL (2017) Aromatic and antiaromatic ring currents in a molecular nanoring. Nature 541:200CrossRefPubMed
3.
Zurück zum Zitat Hoffmann M, Kärnbratt J, Chang M-H, Herz LM, Albinsson B, Anderson HL (2008) Enhanced π conjugation around a porphyrin[6] nanoring. Angew Chem Int Ed 47:4993CrossRef Hoffmann M, Kärnbratt J, Chang M-H, Herz LM, Albinsson B, Anderson HL (2008) Enhanced π conjugation around a porphyrin[6] nanoring. Angew Chem Int Ed 47:4993CrossRef
4.
Zurück zum Zitat O’Sullivan MC, Sprafke JK, Kondratuk DV, Rinfray C, Claridge TD, Saywell A, Blunt MO, O’Shea JN, Beton PH, Malfois M, Anderson HL (2011) Vernier templating and synthesis of a 12-porphyrin nano-ring. Nature 469:72PubMedCrossRef O’Sullivan MC, Sprafke JK, Kondratuk DV, Rinfray C, Claridge TD, Saywell A, Blunt MO, O’Shea JN, Beton PH, Malfois M, Anderson HL (2011) Vernier templating and synthesis of a 12-porphyrin nano-ring. Nature 469:72PubMedCrossRef
5.
Zurück zum Zitat Hoffmann M, Wilson CJ, Odell B, Anderson HL (2007) Template‐directed synthesis of a π‐conjugated porphyrin nanoring. Angew Chem Int Ed 46:3122CrossRef Hoffmann M, Wilson CJ, Odell B, Anderson HL (2007) Template‐directed synthesis of a π‐conjugated porphyrin nanoring. Angew Chem Int Ed 46:3122CrossRef
6.
Zurück zum Zitat Kondratuk DV, Perdigao LMA, O’Sullivan MC, Svatek S, Smith G, O’Shea JN, Beton PH, Anderson HL (2012) Two vernier‐templated routes to a 24‐porphyrin nanoring. Angew Chem Int Ed 51:6696CrossRef Kondratuk DV, Perdigao LMA, O’Sullivan MC, Svatek S, Smith G, O’Shea JN, Beton PH, Anderson HL (2012) Two vernier‐templated routes to a 24‐porphyrin nanoring. Angew Chem Int Ed 51:6696CrossRef
7.
Zurück zum Zitat Kondratuk DV, Perdigão LMA, Esmail AMS, O’Shea JN, Beton PH, Anderson HL (2015) Supramolecular nesting of cyclic polymers. Nat Chem 7:317PubMedCrossRef Kondratuk DV, Perdigão LMA, Esmail AMS, O’Shea JN, Beton PH, Anderson HL (2015) Supramolecular nesting of cyclic polymers. Nat Chem 7:317PubMedCrossRef
8.
Zurück zum Zitat Neuhaus P, Cnossen A, Gong JQ, Herz LM, Anderson HL (2015) A molecular nanotube with three‐dimensional π‐conjugation. Angew Chem Int Ed 54:7344CrossRef Neuhaus P, Cnossen A, Gong JQ, Herz LM, Anderson HL (2015) A molecular nanotube with three‐dimensional π‐conjugation. Angew Chem Int Ed 54:7344CrossRef
9.
Zurück zum Zitat Favereau L, Cnossen A, Kelber JB, Gong JQ, Oetterli RM, Cremers J, Herz LM, Anderson HL (2015) Six-coordinate zinc porphyrins for template-directed synthesis of spiro-fused nanorings. J Am Chem Soc 137:14256PubMedPubMedCentralCrossRef Favereau L, Cnossen A, Kelber JB, Gong JQ, Oetterli RM, Cremers J, Herz LM, Anderson HL (2015) Six-coordinate zinc porphyrins for template-directed synthesis of spiro-fused nanorings. J Am Chem Soc 137:14256PubMedPubMedCentralCrossRef
10.
Zurück zum Zitat Kroto HW, Heath JR, O’Brien SC, Curl RF, Smalley RE (1985) C60: buckminsterfullerene. Nature 318:162CrossRef Kroto HW, Heath JR, O’Brien SC, Curl RF, Smalley RE (1985) C60: buckminsterfullerene. Nature 318:162CrossRef
11.
Zurück zum Zitat Scott LT, Boorum MM, McMahon BJ, Hagen S, Mack J, Blank J, Wegner H, de Meijere A (2002) A rational chemical synthesis of C60. Science 295:1500PubMedCrossRef Scott LT, Boorum MM, McMahon BJ, Hagen S, Mack J, Blank J, Wegner H, de Meijere A (2002) A rational chemical synthesis of C60. Science 295:1500PubMedCrossRef
12.
Zurück zum Zitat Kabdulov M, Jansen M, Amsharov KY (2013) Bottom‐up C60 fullerene construction from a fluorinated C60H21F9 precursor by laser‐induced tandem cyclization. Chem Eur J 19:17262PubMedCrossRef Kabdulov M, Jansen M, Amsharov KY (2013) Bottom‐up C60 fullerene construction from a fluorinated C60H21F9 precursor by laser‐induced tandem cyclization. Chem Eur J 19:17262PubMedCrossRef
13.
Zurück zum Zitat Greisch J-F, Amsharov KY, Weippert J, Weis P, Böttcher A, Kappes MM (2016) From planar to cage in 15 easy steps: resolving the C60H21F9– → C60– transformation by ion mobility mass spectrometry. J Am Chem Soc 138:11254PubMedCrossRef Greisch J-F, Amsharov KY, Weippert J, Weis P, Böttcher A, Kappes MM (2016) From planar to cage in 15 easy steps: resolving the C60H21F9 → C60 transformation by ion mobility mass spectrometry. J Am Chem Soc 138:11254PubMedCrossRef
14.
Zurück zum Zitat Matsui K, Segawa Y, Namikawa T, Kamada K, Itami K (2013) Synthesis and properties of all-benzene carbon nanocages: a junction unit of branched carbon nanotubes. Chem Sci 4:84CrossRef Matsui K, Segawa Y, Namikawa T, Kamada K, Itami K (2013) Synthesis and properties of all-benzene carbon nanocages: a junction unit of branched carbon nanotubes. Chem Sci 4:84CrossRef
15.
Zurück zum Zitat Kayahara E, Iwamoto T, Takaya H, Suzuki T, Fujitsuka M, Majima T, Yasuda N, Matsuyama N, Seki S, Yamago S (2013) Synthesis and physical properties of a ball-like three-dimensional π-conjugated molecule. Nat Commun 4:2694PubMedCrossRef Kayahara E, Iwamoto T, Takaya H, Suzuki T, Fujitsuka M, Majima T, Yasuda N, Matsuyama N, Seki S, Yamago S (2013) Synthesis and physical properties of a ball-like three-dimensional π-conjugated molecule. Nat Commun 4:2694PubMedCrossRef
16.
Zurück zum Zitat Matsui K, Segawa Y, Itami K (2014) All-benzene carbon nanocages: size-selective synthesis, photophysical properties, and crystal structure. J Am Chem Soc 136:16452PubMedCrossRef Matsui K, Segawa Y, Itami K (2014) All-benzene carbon nanocages: size-selective synthesis, photophysical properties, and crystal structure. J Am Chem Soc 136:16452PubMedCrossRef
17.
Zurück zum Zitat Ikemoto K, Kobayashi R, Sato S, Isobe H (2017) Synthesis and bowl‐in‐bowl assembly of a geodesic phenylene bowl. Angew Chem Int Ed 56:6511CrossRef Ikemoto K, Kobayashi R, Sato S, Isobe H (2017) Synthesis and bowl‐in‐bowl assembly of a geodesic phenylene bowl. Angew Chem Int Ed 56:6511CrossRef
18.
Zurück zum Zitat Gutzler R, Perepichka DF (2013) π-electron conjugation in two dimensions. J Am Chem Soc 135:16585PubMedCrossRef Gutzler R, Perepichka DF (2013) π-electron conjugation in two dimensions. J Am Chem Soc 135:16585PubMedCrossRef
19.
Zurück zum Zitat Peeks MD, Tait CE, Neuhaus P, Fischer GM, Hoffmann M, Haver R, Cnossen A, Harmer JR, Timmel CR, Anderson HL (2017) Electronic delocalization in the radical cations of porphyrin oligomer molecular wires. J Am Chem Soc 139:10461PubMedPubMedCentralCrossRef Peeks MD, Tait CE, Neuhaus P, Fischer GM, Hoffmann M, Haver R, Cnossen A, Harmer JR, Timmel CR, Anderson HL (2017) Electronic delocalization in the radical cations of porphyrin oligomer molecular wires. J Am Chem Soc 139:10461PubMedPubMedCentralCrossRef
20.
Zurück zum Zitat Ball M, Zhong Y, Fowler B, Zhang B, Li P, Etkin G, Paley DW, Decatur J, Dalsania AK, Li H, Xiao S, Ng F, Steigerwald ML, Nuckolls C (2016) Macrocyclization in the design of organic n-type electronic materials. J Am Chem Soc 138:12861PubMedCrossRef Ball M, Zhong Y, Fowler B, Zhang B, Li P, Etkin G, Paley DW, Decatur J, Dalsania AK, Li H, Xiao S, Ng F, Steigerwald ML, Nuckolls C (2016) Macrocyclization in the design of organic n-type electronic materials. J Am Chem Soc 138:12861PubMedCrossRef
21.
Zurück zum Zitat Zhang G, Mastalerz M (1934) Organic cage compounds—from shape-persistency to function. Chem Soc Rev 2014:43 Zhang G, Mastalerz M (1934) Organic cage compounds—from shape-persistency to function. Chem Soc Rev 2014:43
22.
Zurück zum Zitat Hasell T, Cooper AI (2016) Porous organic cages: soluble, modular and molecular pores. Nat Rev Mater 1:16053CrossRef Hasell T, Cooper AI (2016) Porous organic cages: soluble, modular and molecular pores. Nat Rev Mater 1:16053CrossRef
23.
Zurück zum Zitat Olenyuk B, Levin MD, Whiteford JA, Shield JE, Stang PJ (1999) Self-assembly of nanoscopic dodecahedra from 50 predesigned components. J Am Chem Soc 121:10434CrossRef Olenyuk B, Levin MD, Whiteford JA, Shield JE, Stang PJ (1999) Self-assembly of nanoscopic dodecahedra from 50 predesigned components. J Am Chem Soc 121:10434CrossRef
24.
Zurück zum Zitat Sun Q-F, Iwasa J, Ogawa D, Ishido Y, Sato S, Ozeki T, Sei Y, Yamaguchi K, Fujita M (2010) Self-assembled M24L48 polyhedra and their sharp structural switch upon subtle ligand variation. Science 328:1144PubMedCrossRef Sun Q-F, Iwasa J, Ogawa D, Ishido Y, Sato S, Ozeki T, Sei Y, Yamaguchi K, Fujita M (2010) Self-assembled M24L48 polyhedra and their sharp structural switch upon subtle ligand variation. Science 328:1144PubMedCrossRef
25.
Zurück zum Zitat Zarra S, Wood DM, Roberts DA, Nitschke JR (2015) Molecular containers in complex chemical systems. Chem Soc Rev 44:419PubMedCrossRef Zarra S, Wood DM, Roberts DA, Nitschke JR (2015) Molecular containers in complex chemical systems. Chem Soc Rev 44:419PubMedCrossRef
26.
Zurück zum Zitat Zhang G, Presly O, White F, Oppel IM, Mastalerz M (2014) A shape‐persistent quadruply interlocked giant cage catenane with two distinct pores in the solid state. Angew Chem Int Ed 53:5126 Zhang G, Presly O, White F, Oppel IM, Mastalerz M (2014) A shape‐persistent quadruply interlocked giant cage catenane with two distinct pores in the solid state. Angew Chem Int Ed 53:5126
27.
Zurück zum Zitat Rue NM, Sun J, Warmuth R (2011) Polyimine container molecules and nanocapsules. Isr J Chem 51:743CrossRef Rue NM, Sun J, Warmuth R (2011) Polyimine container molecules and nanocapsules. Isr J Chem 51:743CrossRef
28.
Zurück zum Zitat Zhu B, Chen H, Lin W, Ye Y, Wu J, Li S (2014) Template-directed synthesis of flexible porphyrin nanocage and nanorings via one-step olefin metathesis. J Am Chem Soc 136:15126PubMedCrossRef Zhu B, Chen H, Lin W, Ye Y, Wu J, Li S (2014) Template-directed synthesis of flexible porphyrin nanocage and nanorings via one-step olefin metathesis. J Am Chem Soc 136:15126PubMedCrossRef
29.
Zurück zum Zitat Zhang C, Wang Q, Long H, Zhang W (2011) A highly C70 selective shape-persistent rectangular prism constructed through one-step alkyne metathesis. J Am Chem Soc 133:20995PubMedCrossRef Zhang C, Wang Q, Long H, Zhang W (2011) A highly C70 selective shape-persistent rectangular prism constructed through one-step alkyne metathesis. J Am Chem Soc 133:20995PubMedCrossRef
30.
Zurück zum Zitat Lee S, Yang A, Moneypenny TP, Moore JS (2016) Kinetically trapped tetrahedral cages via alkyne metathesis. J Am Chem Soc 138:2182PubMedCrossRef Lee S, Yang A, Moneypenny TP, Moore JS (2016) Kinetically trapped tetrahedral cages via alkyne metathesis. J Am Chem Soc 138:2182PubMedCrossRef
31.
Zurück zum Zitat Anderson S, Anderson HL, Sanders JKM (1993) Expanding roles for templates in synthesis. Acc Chem Res 26:469CrossRef Anderson S, Anderson HL, Sanders JKM (1993) Expanding roles for templates in synthesis. Acc Chem Res 26:469CrossRef
32.
Zurück zum Zitat Wasielewski MR (2009) Self-assembly strategies for integrating light harvesting and charge separation in artificial photosynthetic systems. Acc Chem Res 42:1910 Wasielewski MR (2009) Self-assembly strategies for integrating light harvesting and charge separation in artificial photosynthetic systems. Acc Chem Res 42:1910
33.
Zurück zum Zitat Aratani N, Kim D, Osuka A (2009) Discrete cyclic porphyrin arrays as artificial light-harvesting antenna. Acc Chem Res 42:1922 Aratani N, Kim D, Osuka A (2009) Discrete cyclic porphyrin arrays as artificial light-harvesting antenna. Acc Chem Res 42:1922
34.
Zurück zum Zitat Parkinson P, Kondratuk DV, Menelaou C, Gong JQ, Anderson HL, Herz LM (2014) Chromophores in molecular nanorings: when is a ring a ring?. J Phys Chem Lett 5:4356PubMedCrossRef Parkinson P, Kondratuk DV, Menelaou C, Gong JQ, Anderson HL, Herz LM (2014) Chromophores in molecular nanorings: when is a ring a ring?. J Phys Chem Lett 5:4356PubMedCrossRef
35.
Zurück zum Zitat Screen TEO, Lawton KB, Wilson GS, Dolney N, Ispasoiu R, Goodson T III, Martin SJ, Bradley DDC, Anderson HL (2001) Synthesis and third order nonlinear optics of a new soluble conjugated porphyrin polymer. J Mater Chem 11:312CrossRef Screen TEO, Lawton KB, Wilson GS, Dolney N, Ispasoiu R, Goodson T III, Martin SJ, Bradley DDC, Anderson HL (2001) Synthesis and third order nonlinear optics of a new soluble conjugated porphyrin polymer. J Mater Chem 11:312CrossRef
36.
Zurück zum Zitat Scott Wilson G, Anderson HL (1999) A conjugated triple strand porphyrin array. Chem Commun 1539 Scott Wilson G, Anderson HL (1999) A conjugated triple strand porphyrin array. Chem Commun 1539
37.
Zurück zum Zitat Hogben HJ, Sprafke JK, Hoffmann M, Pawlicki M, Anderson HL (2011) Stepwise effective molarities in porphyrin oligomer complexes: preorganization results in exceptionally strong chelate cooperativity. J Am Chem Soc 133:20962PubMedCrossRef Hogben HJ, Sprafke JK, Hoffmann M, Pawlicki M, Anderson HL (2011) Stepwise effective molarities in porphyrin oligomer complexes: preorganization results in exceptionally strong chelate cooperativity. J Am Chem Soc 133:20962PubMedCrossRef
38.
Zurück zum Zitat Cremers J, Richert S, Kondratuk DV, Claridge TDW, Timmel CR, Anderson HL (2016) Nanorings with copper(II) and zinc(II) centers: forcing copper porphyrins to bind axial ligands in heterometallated oligomers. Chem Sci 7:6961PubMedPubMedCentralCrossRef Cremers J, Richert S, Kondratuk DV, Claridge TDW, Timmel CR, Anderson HL (2016) Nanorings with copper(II) and zinc(II) centers: forcing copper porphyrins to bind axial ligands in heterometallated oligomers. Chem Sci 7:6961PubMedPubMedCentralCrossRef
39.
Zurück zum Zitat Liu P, Neuhaus P, Kondratuk DV, Balaban TS, Anderson HL (2014) Cyclodextrin‐templated porphyrin nanorings. Angew Chem Int Ed 53:7770CrossRef Liu P, Neuhaus P, Kondratuk DV, Balaban TS, Anderson HL (2014) Cyclodextrin‐templated porphyrin nanorings. Angew Chem Int Ed 53:7770CrossRef
40.
Zurück zum Zitat Robinson PT, Pham TN, Uhrı́n D (2004) In phase selective excitation of overlapping multiplets by gradient-enhanced chemical shift selective filters. J Magn Reson 170:97PubMedCrossRef Robinson PT, Pham TN, Uhrı́n D (2004) In phase selective excitation of overlapping multiplets by gradient-enhanced chemical shift selective filters. J Magn Reson 170:97PubMedCrossRef
41.
Zurück zum Zitat Duncan SJ, Lewis R, Bernstein MA, Sandor P (2007) Selective excitation of overlapping multiplets; the application of doubly selective and chemical shift filter experiments to complex NMR spectra. Magn Reson Chem 45:283PubMedCrossRef Duncan SJ, Lewis R, Bernstein MA, Sandor P (2007) Selective excitation of overlapping multiplets; the application of doubly selective and chemical shift filter experiments to complex NMR spectra. Magn Reson Chem 45:283PubMedCrossRef
42.
Zurück zum Zitat Rousseaux SAL, Gong JQ, Haver R, Odell B, Claridge TDW, Herz LM, Anderson HL (2015) Self-assembly of Russian doll concentric porphyrin nanorings. J Am Chem Soc 137:12713PubMedPubMedCentralCrossRef Rousseaux SAL, Gong JQ, Haver R, Odell B, Claridge TDW, Herz LM, Anderson HL (2015) Self-assembly of Russian doll concentric porphyrin nanorings. J Am Chem Soc 137:12713PubMedPubMedCentralCrossRef
43.
Zurück zum Zitat Liu S, Kondratuk DV, Rousseaux SAL, Gil-Ramírez G, O’Sullivan MC, Cremers J, Claridge TDW, Anderson HL (2015) Caterpillar track complexes in template‐directed synthesis and correlated molecular motion. Angew Chem Int Ed 54:5355CrossRef Liu S, Kondratuk DV, Rousseaux SAL, Gil-Ramírez G, O’Sullivan MC, Cremers J, Claridge TDW, Anderson HL (2015) Caterpillar track complexes in template‐directed synthesis and correlated molecular motion. Angew Chem Int Ed 54:5355CrossRef
44.
Zurück zum Zitat Gong JQ, Parkinson P, Kondratuk DV, Gil-Ramírez G, Anderson HL, Herz LM (2015) Structure-directed exciton dynamics in templated molecular nanorings. J Phys Chem C 119:6414CrossRef Gong JQ, Parkinson P, Kondratuk DV, Gil-Ramírez G, Anderson HL, Herz LM (2015) Structure-directed exciton dynamics in templated molecular nanorings. J Phys Chem C 119:6414CrossRef
45.
Zurück zum Zitat Yong C-K, Parkinson P, Kondratuk DV, Chen W-H, Stannard A, Summerfield A, Sprafke JK, O’Sullivan MC, Beton PH, Anderson HL, Herz LM (2015) Ultrafast delocalization of excitation in synthetic light-harvesting nanorings. Chem Sci 6:181PubMedCrossRef Yong C-K, Parkinson P, Kondratuk DV, Chen W-H, Stannard A, Summerfield A, Sprafke JK, O’Sullivan MC, Beton PH, Anderson HL, Herz LM (2015) Ultrafast delocalization of excitation in synthetic light-harvesting nanorings. Chem Sci 6:181PubMedCrossRef
46.
Zurück zum Zitat Sprafke JK, Kondratuk DV, Wykes M, Thompson AL, Hoffmann M, Drevinskas R, Chen W-H, Yong CK, Kärnbratt J, Bullock JE, Malfois M, Wasielewski MR, Albinsson B, Herz LM, Zigmantas D, Beljonne D, Anderson HL (2011) Belt-shaped π-systems: relating geometry to electronic structure in a six-porphyrin nanoring. J Am Chem Soc 133:17262PubMedCrossRef Sprafke JK, Kondratuk DV, Wykes M, Thompson AL, Hoffmann M, Drevinskas R, Chen W-H, Yong CK, Kärnbratt J, Bullock JE, Malfois M, Wasielewski MR, Albinsson B, Herz LM, Zigmantas D, Beljonne D, Anderson HL (2011) Belt-shaped π-systems: relating geometry to electronic structure in a six-porphyrin nanoring. J Am Chem Soc 133:17262PubMedCrossRef
48.
Zurück zum Zitat Fedorov A, Berberan-Santos MN, Lefèvre J-P, Valeur B (1997) Picosecond time-resolved and steady-state studies of the polarization of the fluorescence of C60 and C70. Chem Phys Lett 267:467CrossRef Fedorov A, Berberan-Santos MN, Lefèvre J-P, Valeur B (1997) Picosecond time-resolved and steady-state studies of the polarization of the fluorescence of C60 and C70. Chem Phys Lett 267:467CrossRef
49.
Zurück zum Zitat Kerisit N, Toupet L, Larini P, Perrin L, Guillemin J-C, Trolez Y (2015) Straightforward synthesis of 5‐bromopenta‐2,4‐diynenitrile and its reactivity towards terminal alkynes: a direct access to diene and benzofulvene scaffolds. Chem Eur J 21:6042PubMedCrossRef Kerisit N, Toupet L, Larini P, Perrin L, Guillemin J-C, Trolez Y (2015) Straightforward synthesis of 5‐bromopenta‐2,4‐diynenitrile and its reactivity towards terminal alkynes: a direct access to diene and benzofulvene scaffolds. Chem Eur J 21:6042PubMedCrossRef
50.
Zurück zum Zitat Scott Wilson G, Anderson H (1996) A conjugated triple strand porphyrin array. Chem Commun 16:1539 Scott Wilson G, Anderson H (1996) A conjugated triple strand porphyrin array. Chem Commun 16:1539
51.
Zurück zum Zitat Benson SW (1958) Statistical factors in the correlation of rate constants and equilibrium constants. J Am Chem Soc 80:5151CrossRef Benson SW (1958) Statistical factors in the correlation of rate constants and equilibrium constants. J Am Chem Soc 80:5151CrossRef
52.
Zurück zum Zitat Ercolani G, Piguet C, Borkovec M, Hamacek J (2007) Symmetry numbers and statistical factors in self-assembly and multivalency. J Phys Chem B 111:12195PubMedCrossRef Ercolani G, Piguet C, Borkovec M, Hamacek J (2007) Symmetry numbers and statistical factors in self-assembly and multivalency. J Phys Chem B 111:12195PubMedCrossRef
53.
Zurück zum Zitat Hunter CA, Anderson HL (2009) What is cooperativity?. Angew Chem Int Ed 48:7488CrossRef Hunter CA, Anderson HL (2009) What is cooperativity?. Angew Chem Int Ed 48:7488CrossRef
54.
Zurück zum Zitat Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2013) Gaussian 09. Revision D.01. Software, Wallingford CT Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2013) Gaussian 09. Revision D.01. Software, Wallingford CT
55.
Zurück zum Zitat Becke AD (1993) Density‐functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648CrossRef Becke AD (1993) Density‐functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648CrossRef
56.
Zurück zum Zitat Ditchfield R, Hehre WJ, Pople JA (1971) Self‐consistent molecular‐orbital methods. IX. An extended Gaussian‐type basis for molecular‐orbital studies of organic molecules. J Chem Phys 54:724CrossRef Ditchfield R, Hehre WJ, Pople JA (1971) Self‐consistent molecular‐orbital methods. IX. An extended Gaussian‐type basis for molecular‐orbital studies of organic molecules. J Chem Phys 54:724CrossRef
57.
Zurück zum Zitat Hehre WJ, Ditchfield R, Pople JA (1972) Self—consistent molecular orbital methods. XII. Further extensions of Gaussian—type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 56:2257CrossRef Hehre WJ, Ditchfield R, Pople JA (1972) Self—consistent molecular orbital methods. XII. Further extensions of Gaussian—type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 56:2257CrossRef
58.
Zurück zum Zitat Hariharan PC, Pople JA (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chem Acc 28:213CrossRef Hariharan PC, Pople JA (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chem Acc 28:213CrossRef
59.
Zurück zum Zitat Rassolov VA, Pople JA, Ratner MA, Windus TL (1998) 6-31G* basis set for atoms K through Zn. J Chem Phys 109:1223CrossRef Rassolov VA, Pople JA, Ratner MA, Windus TL (1998) 6-31G* basis set for atoms K through Zn. J Chem Phys 109:1223CrossRef
60.
Zurück zum Zitat Grimme S, Antony J, Ehrlich S, Krieg H (2010) A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys 132:154104PubMedCrossRef Grimme S, Antony J, Ehrlich S, Krieg H (2010) A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys 132:154104PubMedCrossRef
61.
Zurück zum Zitat Valeur P, Berberan-Santos MN (2012) Molecular fluorescence: principles and applications. Wiley, New YorkCrossRef Valeur P, Berberan-Santos MN (2012) Molecular fluorescence: principles and applications. Wiley, New YorkCrossRef
Metadaten
Titel
The Template-Directed Synthesis of a Fully Conjugated 14-Porphyrin Nanoball
verfasst von
Jonathan Cremers
Copyright-Jahr
2020
DOI
https://doi.org/10.1007/978-3-030-39101-0_5

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.