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  • 1.
    Devaraj, Karthik
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Ingner, Fredric
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Sollert, Carina
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Gates, Paul J.
    Univ Bristol, Sch Chem, Cantocks Close, Bristol BS8 1TS, Avon, England.
    Orthaber, Andreas
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Pilarski, Lukasz T.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation2019Ingår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, nr 9, s. 5863-5871Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A new, operationally simple approach is presented to access arynes and their fluoride-activated precursors based on Ru-catalyzed C-H silylation of arylboronates. Chromatographic purification may be deferred until after aryne capture, rendering the arylboronates de facto precursors. Access to various new arynes and their derivatives is demonstrated, including, for the first time, those based on a 2,3-carbazolyne and 2,3-fluorenyne core, which pave the way for novel derivatizations of motifs relevant to materials chemistry.

  • 2.
    Green, Joshua P.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi. Imperial Coll London, Dept Chem, London SW7 2AZ, England.
    Cha, Hyojung
    Imperial Coll London, Dept Chem, London SW7 2AZ, England.
    Shahid, Munazza
    Imperial Coll London, Dept Chem, London SW7 2AZ, England.
    Creamer, Adam
    Imperial Coll London, Dept Chem, London SW7 2AZ, England.
    Durrant, James R.
    Imperial Coll London, Dept Chem, London SW7 2AZ, England.
    Heeney, Martin
    Imperial Coll London, Dept Chem, London SW7 2AZ, England.
    Dithieno[3,2-b:2,3-d]arsole-containing conjugated polymers in organic photovoltaic devices2019Ingår i: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 48, nr 20, s. 6676-6679Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Arsole-derived conjugated polymers are a relatively new class of materials in the field of organic electronics. Herein, we report the synthesis of two new donor polymers containing fused dithieno[3,2-b:2,3-d]arsole units and report their application in bulk heterojunction solar cells for the first time. Devices based upon blends with PC71BM display high open circuit voltages around 0.9 V and demonstrate power conversion efficiencies around 4%.

  • 3.
    Green, Joshua P.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Wells, Jordann A. L.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Orthaber, Andreas
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Heavier pnictogens - treasures for optical electronic and reactivity tuning2019Ingår i: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 48, nr 14, s. 4460-4466Artikel, forskningsöversikt (Refereegranskat)
    Abstract [en]

    We highlight recent advances in organopnictogen chemistry contrasting the properties of lighter and heavier pnictogens. Exploring new bonding situations, discovering unprecedented reactivities and producing fascinating opto-electronic materials are some of the most prominent directions of current organopnicogen research. Expanding the chemical toolbox towards the heavier group 15 elements will continue to create new opportunities to tailor molecular properties for small molecule activation/reactivity and materials applications alike. This frontier article illustrates the elemental substitution approach in selected literature examples.

  • 4.
    Gupta, Arvind Kumar
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Oorganisk kemi. Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Green, Joshua P.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Orthaber, Andreas
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Oorganisk kemi. Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Rearrangement and redistribution reaction of Ph2PCH2TMS with PhAsCl2 or AsCl32019Ingår i: Phosphorus Sulfur and Silicon and the Related Elements, ISSN 1042-6507, E-ISSN 1563-5325, Vol. 194, nr 10, s. 967-971Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The attempted synthesis of bis(diphenylphosphinomethyl) phenylarsane and tris(diphenylphosphinomethyl) arsane through condensation of chloro arsanes and diphenyl (trimethylsilylmethyl) phosphane yielded a number of side products originating from migratory and redox-reactions in addition to the targeted ligands. An unexpected, 1,3,4-phosphadiarssolan-1-ium salt was obtained and crystallographically characterized as an A-shaped chlorido adduct. [GRAPHICS] .

  • 5.
    Gupta, Arvind Kumar
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Morales Salazar, Daniel
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Orthaber, Andreas
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Solvent and Counter-Ion Induced Coordination Environment Changes Towards Ag-I Coordination Polymers2019Ingår i: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, Vol. 2019, nr 33, s. 3740-3744Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A series of silver coordination polymers based on the 9,9 '-bis(4,5-diazafluorene) (BDF-H-2) ligand is presented. The choice of counterions and reaction conditions dictate the observed topology on the final systems by influencing the silver coordination environment. Coordination modes, flexibility of the ligand and extended pi-pi stacking interactions have allowed the preparation and crystallographic characterisation of one 1D- and three 2D-coordination polymers: 1D-[Ag(BDF-H-2)(DMSO)](n)(X)(n) (where X = OTf- and ClO4-); 1D-[Ag-2(BDF-H-2) m(1)-(TfO)(2),m(2)-(TfO)(2)](n)(TfO)(n), and 2D-[Ag-2(BDF-H-2)(3)](n)(PF6)(2n).

  • 6.
    Pammer, Frank
    et al.
    Univ Ulm, Inst Organ Chem & Adv Mat 2, Albert Einstein Allee 11, D-89081 Ulm, Germany.
    Schepper, Jonas
    Univ Ulm, Inst Organ Chem & Adv Mat 2, Albert Einstein Allee 11, D-89081 Ulm, Germany.
    Gloeckler, Johannes
    Univ Ulm, Inst Analyt & Bioanalyt Chem, Albert Einstein Allee 11, D-89081 Ulm, Germany.
    Sun, Yu
    Tech Univ Kaiserslautern, Fachbereich Chem, Erwin Schrodinger Str 54, D-67663 Kaiserslautern, Germany.
    Orthaber, Andreas
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Expansion of the scope of alkylboryl-bridged N -> B-ladder boranes: new substituents and alternative substrates2019Ingår i: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 48, nr 27, s. 10298-10312Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A series of new boranes capable of forming intramolecular N -> B-heterocycles has been prepared and their properties have been studied by electrochemical methods and UV-vis-spectroscopy complemented by DFT calculations. A dimethylborane (BMe2), haloborane derivatives (BBr2, BF2, BI2) and mixed cyano/isocyano-borane (B(CN)(NC)) have been prepared by different techniques. Furthermore, 2 '-alkynyl-substituted 2-phenylpyridines bearing terminal tert-butyl- and trimethylsilyl-groups are introduced as a new class of substrates for hydroboration. Successful hydroboration with either 9H-borabicyclo[3.3.1]-nonane (9H-BBN), dimesitylborane (Mes(2)B-H), or Piers' borane ((C6F5)(2)B-H, BPF-H) furnished new pi-extended boranes capable of forming intramolecular six- or seven-membered N -> B-heterocycles (tBuBBN, SiBPF), and, in the case of Mes(2)BH, formation of a sterically crowded styrylborane (SiBMes(2)) incapable of intramolecular N -> B-coordination was observed. All the boranes listed above except BMe2 have been structurally characterized, and a study of their electrochemical properties showed that the systematic variation of the substituents on boron allows for the incremental variation of the electron affinity of the phenylpyridine-model system over a total range of >0.7 eV between alkylboranes (BMe2, BBN) and B(CN)(NC). B(CN)(NC) shows the strongest N -> B-bond (approximate to 175 kJ mol(-1)), and highest electron-affinity observed so far, and is the first example of a borane bearing an isocyano-substituent on boron.

  • 7.
    Roy, Souvik
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Molekylär biomimetik.
    Huang, Zhehao
    Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden.
    Bhunia, Asamanjoy
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Molekylär biomimetik.
    Castner, Ashleigh
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Gupta, Arvind Kumar
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Zou, Xiaodong
    Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden.
    Ott, Sascha
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Electrocatalytic Hydrogen Evolution from a Cobaloxime-Based Metal-Organic Framework Thin Film2019Ingår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 141, nr 40, s. 15942-15950Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Molecular hydrogen evolution catalysts (HECs) are synthetically tunable and often exhibit high activity, but they are also hampered by stability concerns and practical limitations associated with their use in the homogeneous phase. Their incorporation as integral linker units in metal-organic frameworks (MOFs) can remedy these shortcomings. Moreover, the extended three-dimensional structure of MOFs gives rise to high catalyst loadings per geometric surface area. Herein, we report a new MOF that exclusively consists of cobaloximes, a widely studied HEC, that act as metallo-linkers between hexanuclear zirconium clusters. When grown on conducting substrates and under applied reductive potential, the cobaloxime linkers promote electron transport through the film as well as function as molecular HECs. The obtained turnover numbers are orders of magnitude higher than those of any other comparable cobaloxime system, and the molecular integrity of the cobaloxime catalysts is maintained for at least 18 h of electrocatalysis. Being one of the very few hydrogen evolving electrocatalytic MOFs based on a redox-active metallo-linker, this work explores uncharted terrain for greater catalyst pathways.

  • 8.
    Toldo, Josene
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    El Bakouri, Ouissam
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Sola, Miquel
    Univ Girona, IQCC, C M Aurelia Capmany 69, Girona 17003, Spain;Univ Girona, Dept Quim, C M Aurelia Capmany 69, Girona 17003, Spain.
    Norrby, Per-Ola
    AstraZeneca, Early Prod Dev, Pharmaceut Sci, IMED Biotech Unit, Pepparedsleden 1, S-43183 Molndal, Sweden.
    Ottosson, Henrik
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Is Excited-State Aromaticity a Driving Force for Planarization of Dibenzannelated 8 Π-Electron Heterocycles?2019Ingår i: CHEMPLUSCHEM, ISSN 2192-6506, Vol. 84, nr 6, s. 712-721Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Compounds with dibenzannelated heterocycles with eight pi-electrons are found in a range of applications. These molecules often adopt a bent structure in the ground state (S-0) but can become planar in the first excited states (S-1 and T-1) because of the cyclically conjugated 4n pi central ring, which fulfils the requirements for excited state aromaticity. We report on a quantum chemical investigation of the aromatic character in the S-1 and T-1 states of dibenzannelated seven- and six-membered heterocycles with one, two, or three heteroatoms in the 8 pi-electron ring. These states could have pi pi* or n pi* character. We find that compounds with one or two heteroatoms in the central ring have pi pi* states as their S-1 and T-1 states. They are to a significant degree influenced by excited state aromaticity, and their optimal structures are planar or nearly planar. Among the heteroatoms, nitrogen provides for the strongest excited state aromaticity whereas oxygen provides for the weakest, following the established trend of the S-0 state. Yet, dibenzannelated seven-membered-ring compounds with N=N bonds have non-aromatic n pi* states with strongly puckered structures as their S-1 and T-1 states.

  • 9.
    Vanderkooy, Alan
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Gupta, Arvind Kumar
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Foldes, Tamas
    Hungarian Acad Sci, Inst Organ Chem, Res Ctr Nat Sci, Magyar Tudosok Korutja 2, H-1117 Budapest, Hungary;Kings Coll London, Dept Chem, London SE1 1DB, England.
    Lindblad, Sofia
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Orthaber, Andreas
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Papai, Imre
    Hungarian Acad Sci, Inst Organ Chem, Res Ctr Nat Sci, Magyar Tudosok Korutja 2, H-1117 Budapest, Hungary.
    Erdélyi, Máté
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Halogen Bonding Helicates Encompassing Iodonium Cations2019Ingår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, nr 27, s. 9012-9016Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The first halonium-ion-based helices were designed and synthesized using oligo-aryl/pyridylene-ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix is shorter than the sum of their van der Waals radii. The helical conformations were characterized by X-ray crystallography in the solid state, by NMR spectroscopy in solution and corroborated by DFT calculations. The helical complexes possess potential synthetic utility, as demonstrated by their ability to induce iodocyclization of 4-penten-1-ol.

  • 10.
    Wang, Shihuai
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Fysikalisk kemi.
    Pullen, Sonja
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Molekylär biomimetik. TU Dortmund Univ, Fac Chem & Chem Biol, Otto Hahn Str 6, D-44227 Dortmund, Germany.
    Weippert, Valentin
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström.
    Liu, Tianfei
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Fysikalisk kemi.
    Ott, Sascha
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Lomoth, Reiner
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Fysikalisk kemi.
    Hammarström, Leif
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Fysikalisk kemi.
    Direct Spectroscopic Detection of Key Intermediates and Turnover Process in Catalytic H2 Formation by a Biomimetic Diiron Catalyst2019Ingår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, nr 47, s. 11135-11140Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    [FeFe(Cl-2-bdt)(CO)(6)] (1; Cl-2-bdt=3,6-dichlorobenzene-1,2-dithiolate), inspired by the active site of FeFe-hydrogenase, shows a chemically reversible 2 e(-) reduction at -1.20 V versus the ferrocene/ferrocenium couple. The rigid and aromatic bdt bridging ligand lowers the reduction potential and stabilizes the reduced forms, compared with analogous complexes with aliphatic dithiolates; thus allowing details of the catalytic process to be characterized. Herein, time-resolved IR spectroscopy is used to provide kinetic and structural information on key catalytic intermediates. This includes the doubly reduced, protonated complex 1H(-), which has not been previously identified experimentally. In addition, the first direct spectroscopic observation of the turnover process for a molecular H-2 evolving catalyst is reported, allowing for straightforward determination of the turnover frequency.

  • 11.
    Wang, Vincent Cho-Chien
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Fysikalisk kemi.
    Johnson, Ben A.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Interpreting the Electrocatalytic Voltammetry of Homogeneous Catalysts by the Foot of the Wave Analysis and Its Wider Implications2019Ingår i: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 9, nr 8, s. 7109-7123Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Mechanistic studies of electrocatalytic reactions play a crucial role in developing efficient electrocatalysts and solar-fuel devices. The foot of the wave analysis (FOWA) for cyclic voltammetry, recently developed by Saveant and Costentin, provides a powerful means to evaluate the performance of molecular electrocatalysts. However, there is a considerable amount of confusion in the community on how to interpret FOWA in multielectron electrochemical reactions. Herein, we further expand their earlier models from the Nernstian region to all scenarios (i.e., including non-Nernstian behavior) and systematically examine individual parameters, such as formal potentials and reaction rate constants, to explore deeper insights and limitations. Detailed analysis from in silico voltammograms based on different mechanistic models reveals characteristic features of FOWA traces for different kinetic phenomena, which is useful to diagnose kinetic profiles and elucidate the limits of FOWA. The lessons learned from these analyses are further used to reconcile the discrepancy of rate constants determined by FOWA versus other methods, such as time-resolved spectroscopy, for molecular electrocatalysts that catalyze proton reduction or the reduction of CO2 to CO. Such reconciliation demonstrates that electrochemical methods along with FOWA can serve as an alternative tool to determine kinetic information and probe mechanistic insights, which otherwise may be challenging and complicated to achieve by conventional methods. In addition, general guidelines and warnings are also presented to avoid potential errors or mishandling when using FOWA.

  • 12.
    Xiong, Ruisheng
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Arkhypchuk, Anna I.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Borbas, K. Eszter
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Syntetisk molekylär kemi.
    Attempted syntheses of N-confused hydroporphyrins through modified Lindsey routes2019Ingår i: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 23, nr 4-5, s. 589-598Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Unlike N-confused porphyrins which are well-known and extensively studied tetrapyrroles, N-confused hydroporphyrins are almost unknown, largely because so far they have resisted attempts at rational synthesis. Here, we report our efforts towards the total synthesis of N-confused hydroporphyrins. We have prepared N-confused building blocks analogous to the non-N-confused substrates in the Lindsey synthesis of sparsely substituted chlorins. We have systematically flipped the A, B and C pyrrole rings in the dipyrrolic precursors of the target N-confused macrocycles, preparing in total an N-confused "Western half' (tetrahydrodipyrrin) and two N-confused "Eastern halves" (brominated formyldipyrromethanes). These were subjected to a range of cyclization conditions. While we successfully isolated and identified three macrocyclic products, none of these proved to be the desired N-confused hydroporphyrin.

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