1.1 Porphyrins - Friedrich-Alexander-Universität Erlangen-Nürnberg

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List of Abbreviations Ac acetyl acac acetylacetonate aq. aqueous Ar aryl ATR attenuated total reflection BCKP bis-cycloketo-porphyrin BOC t-butoxycarbonyl Bu butyl COSY correlation spectroscopy δ chemical shift DAFS decay associated fluorescence spectroscopy DCTB trans-2-(3-(4-t-butylphenyl)-2-methyl-2-propenylidene)malononitrile DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone DFT density functional theory DMAP N,N-dimethyl-4-aminopyridine DMF N,N-dimethylformamide DMSO dimethylsulfoxide e electron E energy E (E½) (half-wave) potential ε molar extinction coefficient EA elemental analysis EDC 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide EN (ENG) (group) electronegativity Epa ,Epc anodic (cathodic) peak potential eq. equivalent(s) ET energy transfer / electron transfer Et (EtOH) ethyl (ethanol) exc. excess(ive) FAB+ fast atom bombardment, positive detection mode FC flash column chromatography Fc / Fc + ferrocene / ferrocinium FRET FÖRSTER resonance energy transfer fl fluorescence GP general procedure [H] + protic or LEWIS acid catalyst hν photonic/light energy HOMO highest occupied molecular orbital Hp (HpD) hematoporphyrin (derivative) IC internal conversion IR infra-red ISC intersystem crossing IUPAC international union of pure and applied chemistry
n J j-coupling (constant) with n indicating the number of involved bonds λ wavelength LUMO lowest unoccupied molecular orbital M molecular weight M(X)-1 metal complex of 1, X represents the metal’s oxidation state M molar, mol·L -1 m/z mass per charge MALDI-TOF matrix assisted laser desorption ionization – time of flight Me (MeOH) methyl (methanol) MM + molecular mechanics MRCI multireference configuration interaction MS mass spectrometry NBA m-nitrobenzyl alcohol NHS N-hydroxysuccinimide NMR nuclear magnetic resonance NOE nuclear OVERHAUSER effect Nu nucleophile 1 O2 ( 3 O2) singlet (triplet) oxygen o/m/p ortho / meta / para Ox oxidation P(x) portion of compound x 1 3 P ( P) singlet (triplet) state of a photosensitizer PDT photodynamic therapy PEG polyethylene glycol Φ (ΦΔ) quantum yield (of singlet oxygen generation) PM3 parameterized method No. 3 ppm parts per million r radius R substituent Red reduction rt room temperature Sx singlet state, x = 0, 1, 2… (singlet ground state, first excited singlet state…) SN nucleophilic substitution SCE standard calomel electrode SPR structure-properties-relations Sub (organic) substrate t tertiary T / K thermodynamic temperature in degrees KELVIN Tx triplet state, x = 0, 1, 2… (triplet ground state, first excited triplet state…) τ fluorescence decay time TCSPC time-correlated single photon counting TFA 2,2,2-trifluoroacetic acid θ / °C temperature in degrees CELSIUS THF tetrahydrofuran TLC thin layer chromatography TPP tetraphenylporphyrin UV/Vis ultra violet / visual VT various temperature wt% weight percent
Page 1 and 2: Semi-Natural and Synthetic Chiral C
Page 3 and 4: Die vorliegende Arbeit entstand in
Page 5: Table of Contents 1 Introduction 1
Page 10 and 11: 1 Introduction characteristics. For
Page 12 and 13: 1 Introduction 1.1 Porphyrins - A G
Page 14 and 15: 1 Introduction Especially interesti
Page 16 and 17: 1 Introduction 8 [H] 4 + 4 O H O H
Page 18 and 19: 1 Introduction complexes are usuall
Page 20 and 21: 1 Introduction transitions as it is
Page 22 and 23: 1 Introduction 1.2 Photodynamic The
Page 24 and 25: 1 Introduction Certainly, Photofrin
Page 26 and 27: 1 Introduction intact membranes bei
Page 28 and 29: 1 Introduction components, the limi
Page 30 and 31: 2 State of The Art & Aims They were
Page 32 and 33: 2 State of The Art & Aims 2.2 Aim o
Page 34 and 35: 3 Discussion and Results encapsulat
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Page 40 and 41: 3 Discussion and Results irradiatio
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Page 44 and 45: 3 Discussion and Results 3.2.2.1.2
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3 Discussion and Results 3.2.3.3 Va
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3 Discussion and Results 3.2.3.3.2
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3 Discussion and Results Obviously,
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3 Discussion and Results Like Figur
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3 Discussion and Results utilizatio
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3 Discussion and Results has been d
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3 Discussion and Results other TPP
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3 Discussion and Results (being sup
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3 Discussion and Results other band
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3 Discussion and Results Table 10.
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3 Discussion and Results voltammogr
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3 Discussion and Results 3.2.5 Inhe
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3 Discussion and Results effects 12
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3 Discussion and Results 74 Δθ [m
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3 Discussion and Results 3.2.6.2 10
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3 Discussion and Results vibration
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3 Discussion and Results 3.2.6.4 Sy
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3 Discussion and Results cyanomethy
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3 Discussion and Results 3.2.6.5 Co
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3 Discussion and Results phenyl sub
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3 Discussion and Results 90 5 μA -
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3 Discussion and Results 3.2.7 Appr
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3 Discussion and Results (75 eq.) w
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3 Discussion and Results 3.2.7.2 Sy
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3 Discussion and Results of rotatio
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3 Discussion and Results Thus, the
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3 Discussion and Results Time-resol
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3 Discussion and Results first redu
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3 Discussion and Results correspond
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3 Discussion and Results The remain
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3 Discussion and Results 3.2.8.1 Us
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3 Discussion and Results With all t
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3 Discussion and Results The interm
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3 Discussion and Results 116 HO 2 C
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3 Discussion and Results nitro comp
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3 Discussion and Results The effect
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3 Discussion and Results 3.2.9 Pote
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3 Discussion and Results peak at m/
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3 Discussion and Results Table 25.
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3 Discussion and Results 130
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4 Summary As the characterization d
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5 Zusammenfassung 5 Zusammenfassung
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5 Zusammenfassung Da in guten Ausbe
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6 Experimental Section UV/Vis spect
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6 Experimental Section 6.2 Studied
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6 Experimental Section 13 C NMR (10
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6 Experimental Section (cyanomethyl
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6 Experimental Section 6.2.4 AB3-Ty
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6 Experimental Section 6.2.4.3 5 4
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6 Experimental Section 6.2.4.11 10
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6 Experimental Section EA: C57H56N4
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6 Experimental Section 6.2.4.15 10
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6 Experimental Section 6.2.5 A2B2-T
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6 Experimental Section 6.2.5.5 αβ
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6 Experimental Section 6.2.5.7 αβ
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6 Experimental Section 6.2.5.9 αα
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6 Experimental Section 6.2.5.11 α
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6 Experimental Section 6.2.5.13 α
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6 Experimental Section 6.2.6 AB2C-T
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6 Experimental Section UV/Vis (CH2C
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6 Experimental Section UV/Vis (CH2C
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6 Experimental Section broad signal
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7 References 16 H. Fischer, K. Zeil
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7 References 57 S. Schwartz, K. Abs
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7 References 89 (a) R. C. Fuson, J.
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7 References 131 (a) J. Perdew, Phy
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S. Jasinski, N. Jux, “Investigati
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Ein großer Dank gilt auch den Ange
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Cirruculum vitae Stefan Jasinski Ge
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1.1 Porphyrins - Friedrich-Alexander-Universität Erlangen-Nürnberg

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