Pyrrole Units Research Articles

Design, synthesis, photophysical properties and intrinsic mechanism of two difluoroboron β-diketonate complexes with TPE and N-alkyl pyrrole units

It is a hot topic to furnish aggregation-caused quenching luminogens with aggregation-induced emission (AIE) active units and explore their optical properties and inherent mechanism. In this paper, two newly designed and synthesized difluoroboron β-diketonate complexes (TPE-BF2-2AP and TPE-BF2-2MP) with tetra (phenyl) ethylene (TPE) and N-alkyl pyrrole unit exhibit solvatochromism, AIE and mechanochromic properties. Although the alkyl substituents with slight difference, TPE-BF2-2AP relative to TPE-BF2-2MP show distinct increased stokes shift and red shifted fluorescence emission in organic solvents. More interestingly, single crystal analysis reveals that TPE-BF2-2MP forms head-to-head anti-parallel stacking, while TPE-BF2-2AP adopts a scarce head-to-head cross non-parallel stacking, leading to enhanced quantum efficiency from 0.24 to 0.34 before/after grinding, and blue shifted fluorescence emission compared with TPE-BF2-2MP in aggregated states and crystalline states. In addition, the two luminogens exhibit multi-state emission properties by grinding, solvent fumigation and heating due to incomplete transformation between amorphous and crystalline state.

Shaping a Porphyrinoid Frame by Heteroatoms Extrusion: Formation of an Expanded [22]Triphyrin(6.6.0).

An aromatic expanded triphyrin, [22]triphyrin(6.6.0) 2, containing a pyrrole unit, a bipyrrole moiety, and annulene links, was obtained from a tellurium-containing precursor meso-tetraaryl-26,28-ditellurasapphyrin 1. The reaction path proceeds through an acid-promoted tellurium extrusion from 1 yielding directly 2, characterized in a dicationic form by X-ray crystallography. In solution the neutral macrocycle 2 reveals flexibility typical for annulenes and it exists as a mixture of conformers that differ by the configuration of the annulene fragments, as proven by 1 H NMR studies and analyzed by DFT methods. The conformation is controlled by protonation state, the nature of an interacting anion, solvent identity, and by interaction with water.

Isolation, characterization, and antioxidative activity of a dioxobilin-type phylloxanthobilin from savoy cabbage

The degradation of the green pigment chlorophyll in plants is known to yield phyllobilins as highly abundant linear tetrapyrroles. Recently, a split path of the degradation pathway has been discovered, leading to so-called dioxobilin-type (or type-II) phyllobilins. The first characterized type-II phyllobilin was colorless featuring four deconjugated pyrrole units. Similar to the type-I branch, for which yellow oxidation products of the colorless phyllobilins – the type-I phylloxanthobilins – are known, a type-II phylloxanthobilin has recently been characterized from senescent leaves of grapevine. Type-I phylloxanthobilins appear to be actively produced in the plant, are known to possess interesting chemical properties, and were shown to act as potent antioxidants that can protect cells from oxidative stress. Here we report the isolation and structural characterization of a type-II phylloxanthobilin from de-greened leaves of savoy cabbage, which turned out to be structurally closely related to bilirubin. Bilirubin is known to possess high antioxidative activity; in addition, savoy cabbage is considered to promote health benefits due to its high content in antioxidants. We therefore investigated the in vitro antioxidative potential of the newly identified type-II phylloxanthobilin using two different approaches, both of which revealed an even higher antioxidative activity for the type-II phylloxanthobilin from savoy cabbage compared to bilirubin.

Conjugated random terpolymers based on benzodithiophene, diketopyrrolopyrrole, and 8,10‐bis(thiophen‐2‐yl)‐2,5‐di(nonadecan‐3‐yl)bis[1,3]thiazolo[4,5‐f:5′,4′‐h]thieno[3,4‐b]quinoxaline for Efficient Polymer Solar Cell

ABSTRACTA series of novel donor–acceptor (D–A) random conjugated terpolymers P2‐P4 along with the homopolymers P1 (BDT‐DPP) and P5 (BDT‐BTDQ) were designed and synthesized by copolymerizing a benzo[1,2‐b:4,5‐b]dithiophene (BDT) donor with an electron‐deficient diketopyrrolo[3,4‐c]pyrrole (DPP) unit and a benzothiadiazolo[3,4‐e]quinoxaline (BTDQ) moieties of different electron‐withdrawing strengths, and the resultant terpolymers showed broad absorption profile ranging from 300 to 1200 nm. The HOMO levels of the polymers were adjusted from −5.23 to −5.11 eV, and the optical bandgaps were controlled from 1.32 to 1.13 eV by changing the molar ratio of DPP and BTDQ acceptors. These terpolymers were used as a donor along with PC71BM as an acceptor for the creation of polymer solar cells, and the performance was optimized via variable the donor to acceptor ratio and solvent vapor annealing. The polymer solar cells made from the random terpolymer P3 showed the highest overall power conversion efficiency of (9.27%), which is higher than that for the corresponding homo‐polymers counterparts, that is, P1 (7.27%) and P5 (7.68%). The results demonstrate that the designing of random D‐A1‐D‐A2 terpolymers may be the best approach for efficient polymer solar cells. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1478–1485

Novel Porphyrinoids from α,α-Linked Oligopyrroles

α,α-linked oligopyrroles play a crucial role in the synthesis of expanded porphyrins. The preparation of macrocycles such as porphycenes, amethyrins or cyclopyrroles is based on the coupling or condensation of the proper functionalized bipyrrole or terpyrrole. Although longer α,α-linked oligopyrroles have been reported, their chemical instability has hampered their use as synthetic building blocks. Our group have developed a new family of 2,2’-bipyrroles 1 which possesses a remarkable chemical stability ascribed to the presence of two electron withdrawing groups. Bipyrroles 1 can be easily brominated at the α positions allowing their homologation with pyrrole units by means of palladium catalyzed reactions. This strategy has allowed the concise preparation of quaterpyrrole 2 and sexipyrrole 3. In this presentation, the preparation of these oligomers and their use to synthetize new expanded porphyrins will be discussed. Figure 1

Thiophene-Fused Expanded Porphyrins with π-System Switching

Expanded porphyrins that consist of more than five pyrrole units have attracted much attention because of their unique properties such as a flexible π-conjugation circuit, absorption in the visible to near infrared region, and a variable redox state. Since their optical and photophysical properties can be greatly altered by their π-systems, π-system switching based on expanded porphyrins have attracted much interest. Recently, we designed expanded porphyrins with dithieno[3,4-b:3',4'-d]thiophene (β-DTT) unit, which can be regarded as an alternative to a thiophene-fused pyrrole unit. The β-DTT unit could yield two types of π-networks, one is a macrocyclic π-network with incorporation of the lone pair of the central sulfur atom, and the other is a cross-conjugated π-network without incorporation of the lone pair. Thus we expected that the β-DTT unit would provide a new class of core-modified and aromatic-fused expanded porphyrins with π-system switching. We synthesized octaphyrins with the β-DTT unit and demonstrated that oxidation of sulfur atoms on the β-DTT unit was able to switch the π-network of octaphyrin from a macrocyclic 36π-electron network to a cross-conjugated network. In addition, we also synthesized hexaphyrins with the β-DTT unit and revealed a unique, unprecedented π-system switching between a Möbius cross-conjugated π-system and a Hückel antiaromatic π-system. Therefore, the β-DTT unit is a new effective motif to realize π-system switching of expanded porphyrins.

Conductive Directly Fused Metalloporphyrin Coatings By Chemical Vapour Deposition – from Singly to Triply Fused

Porphyrins, whose central structure is composed of four pyrrole units joined by four methine bridges, have been selected by nature to fulfil the two main catalytic phenomena allowing life, i.e. photosynthesis and respiration. Their remarkable functional properties led to the development of numerous porphyrinic compounds for various technological applications, including catalysis and photocatalysis. Porphyrin’s properties can be adjusted by tuning the central metal ion or the pendant groups located at the meso or beta positions. The properties of porphyrin-based devices are also greatly dependent on their integration mode since porphyrins may be directly used dissolved in a liquid medium, covalently grafted onto a surface, embedded in a matrix or polymerised. Conjugated porphyrin polymers,[1] including directly fused porphyrins,[2] display a cooperative effect promoted by conjugated covalent links between porphyrins that yields superior catalytic performances.[1,2] However, the two main synthetic routes towards conjugated poly(porphyrins), (i) oxidative polymerization using a suitable oxidant or (ii) electrodeposition, are a major drawback to their integration into devices. Indeed, the weak solubility of porphyrin monomers, oligomers and polymers requires the introduction of bulky pendant groups to form conjugated poly(porphyrins) in which the tetrapyrrole moieties responsible for the targeted properties end-up diluted. In this work, we report a straightforward chemical vapour deposition approach for the simultaneous synthesis and deposition of conjugated poly(porphyrin) coatings from a simple and commercially available metalloporphyrin, i.e. nickel(II) 5,15-(diphenyl)porphyrin (NiDPP).[3] Our approach relies on the vapour-phase delivery of NiDPP and an oxidant towards a substrate on which they adsorb and react to form conjugated polymer coatings. The direct fusion of NiDPP is notably demonstrated by ultraviolet-visible-near infrared spectrophotometry (UV-Vis-NIR) and high-resolution mass spectrometry (HRMS). Among the investigated oxidants, FeCl3 appears as the candidate of choice for the oxidative fusion of NiDPP in CVD and control of the reactants ratio alternatively allowed the formation of singly-fused P(NiDPP) coatings or multiply-fused (doubly and triply) P(NiDPP) coatings such as evidenced by HRMS. UV-Vis-NIR and conductivity atomic force microscopy (C-AFM) highlight the strong dependence of the optical absorption and electrical conductivity of the fused NiDPP films on the degree of conjugation, opening up the possibility to tune the optoelectronic properties of the P(NiDPP) coatings. Noticeably, the multiply fused P(NiDPP) tapes in thin film form exhibit an electrical conductivity up to 7·10–1 S·cm–1 coupled an absorption deep in the NIR. Our gas-phase reaction approach considerably simplified the integration of fused metalloporphyrins into devices.[3] Following to the very recent report of the superior catalytic activity of fused copper porphyrin dimers,[2] the oCVD reaction of metalloporphyrins will allow the straightforward preparation of potent heterogeneous single‐site catalysts. [1] J. Chen, P. Wagner, L. Tong, G. G. Wallace, D. L. Officer, G. F. Swiegers – A Porphyrin-Doped Polymer Catalyzes Selective, Light-Assisted Water Oxidation in Seawater – Angew. Chem. Int. Ed. 2012, 51, 1907. [2] D. Khusnutdinova, B. L. Wadsworth, M. Flores, A. M. Beiler, E. A. Reyes Cruz, Y. Zenkov, G. F. Moore – Electrocatalytic Properties of Binuclear Cu(II) Fused Porphyrins for Hydrogen Evolution – ACS Catal. 2018, 8, 9888. [3] G. Bengasi, K. Baba, G. Frache, P. Gratia, K. Heinze, N. D. Boscher – Conductive Fused Porphyrin Tapes on Sensitive Substrates by a Chemical Vapor Deposition Approach – Angew. Chem. Int. Ed. 2018, DOI: 10.1002/anie.201814034. Figure 1

The liquid crystal induced J-type aggregation of diketopyrrolopyrrole derivatives in monolayer

The Langmuir and Langmuir-Blodgett techniques have been widely used for nearly a century for the production of molecular thin layers with controlled packing and intermolecular distances. Unfortunately, the Langmuir layers of non-amphiphilic molecules have unstable and unrepeatable parameters. The addition of chemical compounds such as liquid crystals can stabilize and prevent aggregation in the Langmuir layer. The aim of the study was to obtain and characterize Langmuir and Langmuir-Blodgett layers of selected dithiophene diketopyrrolopyrrole (DPP) derivatives and to improve their parameters by forming mixtures with 4‑octyl‑4′‑cyanobiphenyl (8CB). Two DPPs with alkyl chains symmetrically and asymmetrically attached to pyrrole unit were chosen for the investigation. The Langmuir layer of the asymmetrical DPP was unstable over time. For the symmetrically functionalized DPP, after transferring onto solid substrates, agglomerates formation was clearly seen. For DPPs/8CB mixtures, a significant improvement in stability over time was achieved. The confocal microscopy investigation revealed almost complete removal of agglomerate structures in the symmetrical DPP with 8CB. The results proved the miscibility of components at air/water interface and the stabilizing effect of 8CB on DPPs layers. Furthermore, the addition of 8CB forces DPP J-type aggregation in the Langmuir film. Above all, the stable layers with repeatable parameters, made of indistinctly amphiphilic DPP dyes, were shown to form at the air/water interface and on solid substrates.

On local aromaticity of selected model aza-[n]circulenes (n = 6, 7, 8 and 9): Density functional theoretical study

Abstract A computational study using density functional theory is reported for selected model aza[n]circulenes (n = 6, 7, 8 and 9) and their derivatives consisting of pyrrole and benzene units. Local aromaticity of central rings was discussed and analyzed using theoretical structural indices. Depending on their molecular structures, energies of the highest occupied and lowest unoccupied molecular orbitals change from –5.23 eV to –4.08 eV and from –1.97 eV to –0.41 eV, respectively. Based on B3LYP calculated optimal geometries, electronic structure of molecules and their charge transport properties resulted in the suggestion of three planar molecules containing three or four pyrrole units as potential candidates for p-type semiconductors. Hole drift mobilities for ideal stacked dimers of these potential semiconductors were calculated and they range from 0.94 cm2·V−1·s−1 to 7.33 cm2·V−1·s−1.

Skeletal Rearrangement of Twisted Thia‐Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles

AbstractA hybrid thia‐norhexaphyrin comprising a directly linked N‐confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner‐annulated aromatic macrocycles. Oxidation with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone triggered a cleavage of the C−S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique π‐conjugated products: a thiopyrrolo‐pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur‐free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H‐thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions. Using expanded porphyrin scaffolds, oxidative thiophene cleavage and desulfurization of the hitherto unknown N‐confused core‐modified macrocycles would be a practical approach for developing unique polypyrrolic aromatic macrocycles.

Skeletal Rearrangement of Twisted Thia-Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles.

A hybrid thia-norhexaphyrin comprising a directly linked N-confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner-annulated aromatic macrocycles. Oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone triggered a cleavage of the C-S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique π-conjugated products: a thiopyrrolo-pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur-free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H-thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions. Using expanded porphyrin scaffolds, oxidative thiophene cleavage and desulfurization of the hitherto unknown N-confused core-modified macrocycles would be a practical approach for developing unique polypyrrolic aromatic macrocycles.

Synthesis of Pyrrole-Containing Chiral Spiro Molecules and Their Optical and Chiroptical Properties

Abstract The pyrrole-containing chiral spiro π-conjugated compounds were successfully synthesized from 10,10′-spirobi[indeno[1,2-b][1]benzothiophene] 5,5-dioxide and 5,5,5′,5′-tetraoxide via a sequential inter/intramolecular nucleophilic aromatic substitution with arylamines. The enantiopure ones were also prepared from the enantiopure substrates. UV-vis absorption and photoluminescence spectroscopies and theoretical calculations revealed that the replacement of thiophene unit(s) of 10,10′-spirobi[indeno[1,2-b][1]benzothiophene] with pyrrole unit(s) has a great impact on photophysical properties. The pyrrole-containing chiral spiro π-conjugated compounds exhibited circularly polarized luminescence with a relatively large dissymmetry factor.

Enhancement of the thermoelectric property of nanostructured polyaniline/carbon nanotube composites by introducing pyrrole unit onto polyaniline backbone via a sustainable method

The electrical conductivity of conducting polymer depends strongly on the alignment of the polymer chains, and a fully aligned polymer backbone strongly enhances the conjugation. Herein, the pyrrole unit was introduced onto the polyaniline backbone to improve the alignment of the polyaniline (PANi) main chain. The nanostructured poly(aniline-co-pyrrole) random copolymer (PANiPy) was successfully synthesized via a sustainable method without mechanical agitation. FTIR, Raman and XPS spectra confirmed the strong interaction between the pyrrole and the aniline units. Single wall carbon nanotubes (SWCNTs) were applied to improve the membrane forming performance of insoluble conjugated polymers and the polymer/SWCNT composites were prepared. The SEM results revealed that the synthesized polymer exhibited a nanostructured morphology. Nanostructured PANiPy was well dispersed in the SWCNT bundles and formed a self-assembled layered morphology. The PANiPy/SWCNT composite film achieved the highest power factor of 98.5 μW·m−1·k−2, which was much higher than that most carbon-based thermoelectric composites. The results demonstrated that introducing the pyrrole units onto the PANi backbone was a good strategy to tune the alignment of PANi chain, and the thermoelectric performance of PANi/SWCNT composite was enhanced. Moreover, the experimental procedure is attractive as a sustainable process for materials preparation in chemical engineering.

Synthesis and properties of novel extended BODIPYs with rigid skeletons

Novel extended BODIPYs fused with bicyclo rings were synthesized from bicyclopyrroles by combining Knoevenagel condensation, Suzuki coupling, and O-chelation. The absorption maxima of the BODIPYs ranged from the visible to near-infrared region and the compounds showed good solubility in organic solvents. The solubility of the bicycloBODIPY with 2-naphthyl groups at the α-position of the pyrrole units was particularly high. Heating converted distyrylBODIPY with bicyclo[2.2.2]octene to benzoBODIPY with absorption (748.5 nm) and fluorescence (775.0 nm) in the near-infrared region.

Meso-Aryl substituted stable unorthodox 5,10-porphodimethenes with α,β and β,β-N-methyl pyrrole connectivities: synthesis and spectroscopic, solid state and theoretical characterization.

A concise and convenient synthetic methodology leading to an unambiguous isolation of two hitherto unknown highly stable single conformers of meso-aryl substituted unorthodox 5,10-porphodimethenes has been developed by the inclusion of N-methyl pyrrole units with α,β and β,β-linkages into the core of heterocyclic macrocycles.

Synthesis and the effect of alkyl chain length on photochromic properties of diarylethene derivatives

A new class of photochromic diarylethenes bearing pyrrole and thiophene units with different length of alkyl chains at 2-position of thiophene rings have been synthesized. Their characteristics, including photochromism and fatigue resistance were investigated systematically, and each diarylethene derivative showed good photochromic properties whether in solution or in PMMA films. The alkyl group moiety was connected directly to the central cyclopentene ring as a heteroaryl unit and availably participated in photoisomerization reaction. And some properties, for example, the conversion ratio in the photostationary state(PSS) and the absorption coefficient of the ring-closed isomers in acetonitrile were significantly affected by the alkyl chain length. The results revealed that substituents of alkyl chain played an important role in the photoisomerization process of diarylethenes.

Poly(azomethine)s Anchored by Cresol and Pyrrole Units: Synthesis, Characterization and Spectroscopy Studies

In this study, poly(azomethine)s with cresol and pyrrole as side chain units were synthesized in three steps. In the first step; symmetrical dialdehyde bromide (DAB), in the second step; symmetrical derivatives (DAB-1 and DAB-2) of DAB using p-cresol and pyrrole, respectively, and in the third step; poly(azomethine-cresol) (P-1) and poly(azomethine-pyrrole) (P-2) were obtained via condensation reaction. Structures of all synthesized compounds were confirmed by FT-IR, UV-Vis, and 1H NMR spectroscopic analyses. Photophysical and electrochemical properties of these compounds were investigated using photoluminescence (PL) and cyclic voltammetry (CV) measurements, respectively. Based on photoluminescence analysis, the multicolor properties of DAB-2, P-1 and P-2 were observed in DMF solution. Additionally, results of thermal studies of TG-DTA and DSC techniques showed they were thermally stable compounds.

Effects of inserting keto-functionalized side-chains instead of imide-functionalized side-chain on the pyrrole backbone of 2,5-bis(2-thienyl)pyrrole-based polymers for organic solar cells

A 2,5-bis(2-thienyl)pyrrole (TPT)-based new monomer unit incorporating the electron-withdrawing 1-decanone (ketone) at the 3- and 4-positions of the pyrrole unit of TPT was prepared. The resulting keto-functionalized TPT unit (≈TPTK) was polymerized with distannyl derivatives of 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene (BDTT), 4,7-bis(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (DTBT), and 3,6-bis(thiophen-2-yl)-2,5-dioctylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DKPP), to obtain three new polymers (P(BDTT-TPTK), P(DTBT-TPTK) and P(DKPP-TPTK)), respectively. The photophysical, electrochemical, and energy conversion efficiency of the TPTK-based polymers were thoroughly studied and compared with those of structurally similar polymers (P(BDTT-TPTI), P(DTBT-TPTI), and P(DKPP-TPTI)) incorporating an imide-functionalized TPT unit (≈ TPTI). Overall, the TPTK-based polymers showed a higher band-gap (Eg ≈ 2.42 eV, 1.92 eV, and 1.42 eV), deeper highest occupied molecular orbital (HOMO ≈ −5.58 eV, −5.48 eV, and −5.31 eV, respectively) energy levels and lower carrier mobilities than those of the corresponding TPTI-based polymers. These combined effects led to relatively poor solar to electrical energy conversion efficiency for TPTK-based polymers compared to those of TPTI-based polymers.

Switching from Negative-Cooperativity to No-Cooperativity in the Binding of Ion-Pair Dimers by a Bis(calix[4]pyrrole) Macrocycle.

We report the synthesis of a macrocyclic receptor containing two di- meso-phenylcalix[4]pyrrole units linked by two triazole spacers. The 1,4-substitution of the 1,2,3-triazole spacers conveys different binding affinities to the two heteroditopic binding sites. These features make the receptor an ideal candidate to investigate allosteric cooperativity in the binding of ion-pair dimers. We probed the interaction of tetraalkylammonium salts (TBA·Cl, TBA·OCN, and MTOA·Cl) with the tetra-heterotopic macrocyclic receptor in chloroform solution using 1H NMR spectroscopic titration experiments. The results obtained show that, at millimolar concentration, the addition of 2 equiv of the salt to the receptor's solution induced the quantitative pairwise binding of the ion-pairs. The 2:1 (ion-pair:receptor) complexes feature different binding geometries and binding cooperativities depending on the nature of the alkylammonium cation. The binding geometries assigned to the complexes of the ion-pair dimers in solution are fully supported by X-ray diffraction analyses of single crystals. The thermodynamic features of the binding processes (separate or concomitant formation of 1:1 and 2:1 complexes), derived from isothermal titration calorimetry (ITC) experiments, are rationalized by combining the different ion-pair binding modes of the salt dimers with the dissimilar electronic properties of the two nearby heteroditopic binding sites of the receptor.

Synthesis of novel sensitizers with a linear conjugated di(1-benzothieno)[3,2-b:2′,3′-d]pyrrole unit for dye-sensitized solar cells

Three novel D−π−A structural metal-free organic sensitizers (DBTP−1∼3) are designed, in which a linear planar aromatic group, the di(1-benzothieno)[3,2-b:2′,3′-d]pyrrole is first introduced as the π-bridge for dye-sensitized solar cells. Triphenylamine, 9,9-dimethyle-9H-fluorene and carbazole serve as the electron donor, respectively, while cyanoacrylic acid is used as an electron acceptor and anchoring unit. The photophysical, electrochemical, theoretical calculations have been employed to apprehend the correlation between the structures of DBTP−1∼3 and their photovoltaic performances. Further, co-adsorption studies are used to investigate the electronic recombination of the target dyes. As a result, the maximum power conversion efficiency of 6.50% (short-circuit current of 14.66 mA cm−2, open-circuit voltage of 0.67 V, and fill factor of 66%) for the 2 mM chenodeoxycholic acid co-adsorbed device based on DBTP−1 is obtained, while without any co-adsorbent it gives efficiency of 4.55%. The standard dye N719 gives 8.54% power conversion efficiency.