Small Organic Cations Research Articles

Impact of Difluoromethylornithine and AMXT 1501 on Gene Expression and Capsule Regulation in Streptococcus pneumoniae.

Streptococcus pneumoniae (Spn), a Gram-positive bacterium, poses a significant threat to human health, causing mild respiratory infections to severe invasive conditions. Despite the availability of vaccines, challenges persist due to serotype replacement and antibiotic resistance, emphasizing the need for alternative therapeutic strategies. This study explores the intriguing role of polyamines, ubiquitous, small organic cations, in modulating virulence factors, especially the capsule, a crucial determinant of Spn's pathogenicity. Using chemical inhibitors, difluoromethylornithine (DFMO) and AMXT 1501, this research unveils distinct regulatory effects on the gene expression of the Spn D39 serotype in response to altered polyamine homeostasis. DFMO inhibits polyamine biosynthesis, disrupting pathways associated with glucose import and the interconversion of sugars. In contrast, AMXT 1501, targeting polyamine transport, enhances the expression of polyamine and glucose biosynthesis genes, presenting a novel avenue for regulating the capsule independent of glucose availability. Despite ample glucose availability, AMXT 1501 treatment downregulates the glycolytic pathway, fatty acid synthesis, and ATP synthase, crucial for energy production, while upregulating two-component systems responsible for stress management. This suggests a potential shutdown of energy production and capsule biosynthesis, redirecting resources towards stress management. Following DFMO and AMXT 1501 treatments, countermeasures, such as upregulation of stress response genes and ribosomal protein, were observed but appear to be insufficient to overcome the deleterious effects on capsule production. This study highlights the complexity of polyamine-mediated regulation in S. pneumoniae, particularly capsule biosynthesis. Our findings offer valuable insights into potential therapeutic targets for modulating capsules in a polyamine-dependent manner, a promising avenue for intervention against S. pneumoniae infections.

Front-contact passivation through 2D/3D perovskite heterojunctions enables efficient bifacial perovskite/silicon tandem solar cells

•Non-uniform formation of n = 2 is more dominant for iso-BAI-passivated perovskite •Bifacial perovskite/Si tandem devices exhibited power generation density >27 mW cm−2 •Shorter spacer iso-BA reduced the charge accumulation at thinner quantum wells •Branched BA-based 2D perovskite formation resulted in JSC as high as 22.8 mA cm−2 Surface passivation by thin-slab 2D perovskites is an effective method to suppress interfacial carrier recombination of 3D metal halide perovskite photoabsorbers. However, improving device performance by integrating such 2D/3D perovskite heterojunctions in the sunward, transparent contacts of perovskite solar cells is not evident due to the high exciton binding energies of phase-pure 2D perovskites, which may result in inefficient free-carrier generation and collection. Here, we overcome this challenge by tuning the dimensionality of 2D perovskites via structural isomers of butylammonium (BA) as a small organic cation, occupying the A-site of the 2D perovskite lattice. The discontinuous iso-BA-based 2D crystals on the 3D perovskite surface yield improved interfacial passivation and enhanced hole extraction. Besides an increased open circuit voltage, this remarkably leads to an enhanced photocurrent (∼1 mA cm−2) compared with control perovskite solar cells, resulting in bifacial perovskite/silicon tandem solar cells with power generation densities >27 mW cm−2. Surface passivation by thin-slab 2D perovskites is an effective method to suppress interfacial carrier recombination of 3D metal halide perovskite photoabsorbers. However, improving device performance by integrating such 2D/3D perovskite heterojunctions in the sunward, transparent contacts of perovskite solar cells is not evident due to the high exciton binding energies of phase-pure 2D perovskites, which may result in inefficient free-carrier generation and collection. Here, we overcome this challenge by tuning the dimensionality of 2D perovskites via structural isomers of butylammonium (BA) as a small organic cation, occupying the A-site of the 2D perovskite lattice. The discontinuous iso-BA-based 2D crystals on the 3D perovskite surface yield improved interfacial passivation and enhanced hole extraction. Besides an increased open circuit voltage, this remarkably leads to an enhanced photocurrent (∼1 mA cm−2) compared with control perovskite solar cells, resulting in bifacial perovskite/silicon tandem solar cells with power generation densities >27 mW cm−2.

Analysis of gene expression related to polyamine concentration and dimorphism induced in ornithine decarboxylase (odc) and spermidine synthase (spd) Ustilago maydis mutants

Polyamines are ubiquitous small organic cations, and their roles as regulators of several cellular processes are widely recognized. They are implicated in the key stages of the fungal life cycle. Ustilago maydis is a phytopathogenic fungus, the causal agent of common smut of maize and a model system to understand dimorphism and virulence. U. maydis grows in yeast form at pH 7 and it can develop its mycelial form in vitro at pH 3. Δodc mutants that are unable to synthesize polyamines, grow as yeast at pH 3 with a low putrescine concentration, and to complete its dimorphic transition high putrescine concentration is require. Δspd mutants require spermidine to grow and cannot form mycelium at pH 3. In this work, the increased expression of the mating genes, mfa1 and mfa2, on Δodc mutants, was related to high putrescine concentration. Global gene expression analysis comparisons of Δodc and Δspd U. maydis mutants indicated that 2,959 genes were differentially expressed in the presence of exogenous putrescine at pH 7 and 475 genes at pH 3. While, in Δspd mutant, the expression of 1,426 genes was affected by exogenous spermine concentration at pH 7 and 11 genes at pH 3. Additionally, we identified 28 transcriptional modules with correlated expression during seven tested conditions: mutant genotype, morphology (yeast, and mycelium), pH, and putrescine or spermidine concentration. Furthermore, significant differences in transcript levels were noted for genes in modules relating to pH and genotype genes involved in ribosome biogenesis, mitochondrial oxidative phosphorylation, N-glycan synthesis, and Glycosylphosphatidylinositol (GPI)-anchor. In summary, our results offer a valuable tool for the identification of potential factors involved in phenomena related to polyamines and dimorphism.

Controlled Growth of Hybrid Halide Perovskites by Crown Ether Complexation for Perovskite Solar Cells

AbstractHost‐guest complexation has demonstrated potential for controlling hybrid organic‐inorganic metal halide perovskite materials. In particular, crown ethers have been used due to their capacity to interact with metal cations (e. g., Pb2+) and small organic cations (e. g., methylammonium (MA)), which can affect hybrid perovskite materials and their solar cells. However, this strategy has been underexploited in perovskite photovoltaics, and the underlying mechanisms are not well understood. In this study, we investigate the influence of 15‐crown‐5 (15C5) and its benzannulated derivative (benzo‐15‐crown‐5, B15C5), as well as amino‐functionalized analogues (15‐crown‐5)‐2‐methylamine, 2A‐15C5, and 4′‐aminobenzo‐15‐crown‐5, 4A‐B15C5, on MAPbI3 perovskite crystallization and inverted solar cell performance. We demonstrate the propensity of crown ether modulators to interact with Pb2+ cations at the perovskite interface by density functional theory calculations. This has been shown to facilitate oriented crystal growth and homogeneous film formation, as revealed by X‐ray diffraction analysis complemented by scanning electron microscopy. As a result, we demonstrate an increase in the power conversion efficiency of the solar cells of interest to advancing hybrid photovoltaics.

Acquiring a Newly Tailored 2D Dion–Jacobson Hybrid Perovskite with Large Structural Distortion for Efficient Crystal Array Photodetector

AbstractDion–Jacobson (DJ) phase of 2D hybrid perovskites has recently attracted intensive attention owing to their remarkable optoelectronic properties and superior structural stability. In spite of great endeavors, only a few DJ‐type multilayered hybrid perovskites are obtained and most of them are constructed by very small organic spacer cations (e.g., Cs+ and CH3NH3+). It is still challenging to incorporate larger spacing moieties inside the perovskite cages for accomplishing excellent photoelectric properties. Herein, a newly tailored member of DJ‐type 2D perovskites, (HIS)(DMA)Pb2Br7 (1, where HIS2+ is histammonium and DMA+ is dimethylammonium), of which the perovskite cavities display a remarkable structural distortion to accommodate relatively larger secondary DMA+ cation as the “perovskitizer” is acquired. The monolayers of divalent HIS2+ organic cations directly link to inorganic sheets through NH∙∙∙Br hydrogen bonds, thus eliminating the van der Waals gap in 2D Ruddlesden–Popper counterparts and enabling superior phase stability. As a result, crystal‐based array photodetector of 1 shows fascinating photoactive activities of high detectivity (1.2 × 1013 Jones), large responsivity (18.1 A W−1), and antifatigue behavior, along with polarization‐sensitive detection based on the intrinsic anisotropy. Such findings disclose the potential of 1 for efficient photodetection, and definitely enrich the booming family of 2D hybrid perovskites.

Elucidating the Role of Chmp1 Overexpression in the Transport of Polyamines in Drosophila melanogaster.

Polyamines are small organic cations that are essential for many biological processes such as cell proliferation and cell cycle progression. While the metabolism of polyamines has been well studied, the mechanisms by which polyamines are transported into and out of cells are poorly understood. Here, we describe a novel role of Chmp1, a vesicular trafficking protein, in the transport of polyamines using a well-defined leg imaginal disc assay in Drosophila melanogaster larvae. We show that Chmp1 overexpression had no effect on leg development in Drosophila, but does attenuate the negative impact on leg development of Ant44, a cytotoxic drug known to enter cells through the polyamine transport system (PTS), suggesting that the overexpression of Chmp1 downregulated the PTS. Moreover, we showed that the addition of spermine did not rescue the leg development in Chmp1-overexpressing leg discs treated with difluoromethylornithine (DFMO), an inhibitor of polyamine metabolism, while putrescine and spermidine did, suggesting that there may be unique mechanisms of import for individual polyamines. Thus, our data provide novel insight into the underlying mechanisms that are involved in polyamine transport and highlight the utility of the Drosophila imaginal disc assay as a fast and easy way to study potential players involved in the PTS.

Predicting the photon energy of quasi-2D lead halide perovskites from the precursor composition through machine learning.

Quasi-2D perovskites with the general formula of L2An−1PbnX3n+1 (L = organic spacer cation, A = small organic cation or inorganic cation, X = halide ion, and n ≤ 5) are an emerging kind of luminescent material. Their emission color can be easily tuned by their composition and n value. Accurate prediction of the photon energy before experiments is essential but unpractical based on present studies. Herein, we use machine learning (ML) to explore the quantitative relationship between the photon energies of quasi-2D perovskite materials and their precursor compositions. The random forest (RF) model presents high accuracy in prediction with a root mean square error (RMSE) of ∼0.05 eV on a test set. By feature importance analysis, the composition of the A-site cation is found to be a critical factor affecting the photon energy. Moreover, it is also found that the phase impurity greatly lowers the photon energy and needs to be minimized. Furthermore, the RF model predicts the compositions of quasi-2D perovskites with high photon energies for blue emission. These results highlight the advantage of machine learning in predicting the properties of quasi-2D perovskites before experiments and also providing color tuning directions for experiments.

Aziridinium cation templating 3D lead halide hybrid perovskites.

This study describes the synthesis of the first aziridinium-based compounds, namely hybrid perovskites (AzrH)PbHal3 (where AzrH = aziridinium, Hal = Cl, Br or I). This highly reactive species was stabilized in 3D lead halide frameworks and was found to be a small enough organic cation to promote the formation of semiconducting organo-inorganic materials.

Overlap and Specificity in the Substrate Spectra of Human Monoamine Transporters and Organic Cation Transporters 1, 2, and 3.

Human monoamine transporters (MATs) are cation transporters critically involved in neuronal signal transmission. While inhibitors of MATs have been intensively studied, their substrate spectra have received far less attention. Polyspecific organic cation transporters (OCTs), predominantly known for their role in hepatic and renal drug elimination, are also expressed in the central nervous system and might modulate monoaminergic signaling. Using HEK293 cells overexpressing MATs or OCTs, we compared uptake of 48 compounds, mainly phenethylamine and tryptamine derivatives including matched molecular pairs, across noradrenaline, dopamine and serotonin transporters and OCTs (1, 2, and 3). Generally, MATs showed surprisingly high transport activities for numerous analogs of neurotransmitters, but their substrate spectra were limited by molar mass. Human OCT2 showed the broadest substrate spectrum, and also the highest overlap with MATs substrates. Comparative kinetic analyses revealed that the radiotracer meta-iodobenzylguanidine had the most balanced uptake across all six transporters. Matched molecular pair analyses comparing MAT and OCT uptake using the same methodology could provide a better understanding of structural determinants for high cell uptake by MATs or OCTs. The data may result in a better understanding of pharmacokinetics and toxicokinetics of small molecular organic cations and, possibly, in the development of more specific radiotracers for MATs.

Influence of Temperature on Molecular Adsorption and Transport at Liposome Surfaces Studied by Molecular Dynamics Simulations and Second Harmonic Generation Spectroscopy.

A fundamental understanding of the kinetics and thermodynamics of chemical interactions at the phospholipid bilayer interface is crucial for developing potential drug-delivery applications. Here we use molecular dynamics (MD) simulations and surface-sensitive second harmonic generation (SHG) spectroscopy to study the molecular adsorption and transport of a small organic cation, malachite green (MG), at the surface of 1,2-dioleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (DOPG) liposomes in water at different temperatures. The temperature-dependent adsorption isotherms, obtained by SHG measurements, provide information on adsorbate concentration, free energy of adsorption, and associated changes in enthalpy and entropy, showing that the adsorption process is exothermic, resulting in increased overall entropy. Additionally, the molecular transport kinetics are found to be more rapid under higher temperatures. Corresponding MD simulations are used to calculate the free energy profiles of the adsorption and the molecular orientation distributions of MG at different temperatures, showing excellent agreement with the experimental results.

Structural snapshots of TRPV1 reveal mechanism of polymodal functionality

Many transient receptor potential (TRP) channels respond to diverse stimuli and conditionally conduct small and large cations. Such functional plasticity is presumably enabled by a uniquely dynamic ion selectivity filter that is regulated by physiological agents. What is currently missing is a "photo series" of intermediate structural states that directly address this hypothesis and reveal specific mechanisms behind such dynamic channel regulation. Here, we exploit cryoelectron microscopy (cryo-EM) to visualize conformational transitions of the capsaicin receptor, TRPV1, as a model to understand how dynamic transitions of the selectivity filter in response to algogenic agents, including protons, vanilloid agonists, and peptide toxins, permit permeation by small and large organic cations. These structures also reveal mechanisms governing ligand binding substates, as well as allosteric coupling between key sites that are proximal to the selectivity filter and cytoplasmic gate. These insights suggest a general framework for understanding how TRP channels function as polymodal signal integrators.

The Role of Spermidine Synthase (SpdS) and Spermine Synthase (Sms) in Regulating Triglyceride Storage in Drosophila.

Polyamines are small organic cations that are important for several biological processes such as cell proliferation, cell cycle progression, and apoptosis. The dysregulation of intracellular polyamines is often associated with diseases such as cancer, diabetes, and developmental disorders. Although polyamine metabolism has been well studied, the effects of key enzymes in the polyamine pathway on lipid metabolism are not well understood. Here, we determined metabolic effects resulting from the absence of spermidine synthase (SpdS) and spermine synthase (Sms) in Drosophila. While SpdS mutants developed normally and accumulated triglycerides, Sms mutants had reduced viability and stored less triglyceride than the controls. Interestingly, when decreasing SpdS and Sms, specifically in the fat body, triglyceride storage increased. While there was no difference in triglycerides stored in heads, thoraxes and abdomen fat bodies, abdomen fat body DNA content increased, and protein/DNA decreased in both SpdS- and Sms-RNAi flies, suggesting that fat body-specific knockdown of SpdS and Sms causes the production of smaller fat body cells and triglycerides to accumulate in non-fat body tissues of the abdomen. Together, these data provide support for the role that polyamines play in the regulation of metabolism and can help enhance our understanding of polyamine function in metabolic diseases.

Conformational analysis of two new organotin(IV) structures completed with a CSD survey.

The conformational flexibilities are studied in two new organotin(IV) complexes, namely, trans-dichloridodimethylbis[N,N',N''-tris(2-chlorobenzyl)phosphoric triamide]tin(IV), [Sn(CH3)2(C21H21Cl3N3OP)2Cl2] or Sn(CH3)2Cl2{OP[NHCH2C6H4(2-Cl)]3}2, (I), and bis(dipropylammonium) tetrachloridodimethylstannate(IV), [(CH3CH2CH2)2NH2]2[Sn(CH3)2Cl4], (II), and their analogous structures from the Cambridge Structural Database (CSD). The conformations are considered based on the N-P=O-Sn torsion angles for (I) and the C-C-C-N, C-C-N-C, C-N-C-C and N-C-C-C torsion angles for the two symmetry-independent [CH3CH2CH2NH2CH2CH2CH3]+ cations in (II), and the ±ac±sp±ac (ac = anticlinal and sp = synperiplanar) and ±ap±ap±ap±ap (ap = antiperiplanar) conformations are observed, respectively. In both structures, the four atoms in the corners of the square-planar segment of the octahedral shape around the Sn atom participate in normal hydrogen-bonding interactions as acceptors, which include two O and two Cl atoms for (I), and four Cl atoms for (II). However, the phosphoric triamide ligands block the environment around the Sn atom and limit the hydrogen-bond pattern to form a supramolecular ribbon assembly, while in the presence of small organic cations in (II), a two-dimensional hydrogen-bonded architecture is achieved. The weak interactions π-π, C-H...π and C-Cl...π in (I), and C-H...Cl in (II) do not change the dimensionality of the hydrogen-bond pattern. The 62 CSD structures analogous to (I), i.e. with an SnOPN3 segment (including 83 entries) fall into four categories of conformations based on the N-P=O-Sn torsion angles. The 132 [(CH3CH2CH2)2NH2]+ cations from 85 CSD structures are classified into seven groups based on the torsion angles noted for (II). Most of the CSD structures adopt the same associated conformations noted for (I) and (II). 15 [Sn(CH3)2Cl4]2- anions extracted from the CSD are compared with the structure of (II).

Rigid, biconical hydrogen-bonded dimers that strongly encapsulate cationic guests in solution and the solid state

The octol of a new rigid, tetraarylene-bridged cavitand was investigated for self-assembly behaviour in solution. 1H and DOSY NMR spectroscopic experiments show that the cavitand readily dimerizes through an unusual seam of interdigitated hydrogen-bonds that is resistant to disruption by polar co-solvents. The well-defined cavity encapsulates small cationic guests, but not their neutral counterparts, restricting the conformation of sequestered tetraethylammonium in solution and the solid state.

Structure and Function of the Acetylpolyamine Amidohydrolase from the Deep Earth Halophile Marinobacter subterrani.

Polyamines are small organic cations that are essential for cellular function in all kingdoms of life. Polyamine metabolism is regulated by enzyme-catalyzed acetylation-deacetylation cycles in a fashion similar to the epigenetic regulation of histone function in eukaryotes. Bacterial polyamine deacetylases are particularly intriguing, because these enzymes share the fold and function of eukaryotic histone deacetylases. Recently, acetylpolyamine amidohydrolase from the deep earth halophile Marinobacter subterrani (msAPAH) was described. This Zn2+-dependent deacetylase shares 53% amino acid sequence identity with the acetylpolyamine amidohydrolase from Mycoplana ramosa (mrAPAH) and 22% amino acid sequence identity with the catalytic domain of histone deacetylase 10 from Danio rerio (zebrafish; zHDAC10), the eukaryotic polyamine deacetylase. The X-ray crystal structure of msAPAH, determined in complexes with seven different inhibitors as well as the acetate coproduct, shows how the chemical strategy of Zn2+-dependent amide hydrolysis and the catalytic specificity for cationic polyamine substrates is conserved in a subterranean halophile. Structural comparisons with mrAPAH reveal that an array of aspartate and glutamate residues unique to msAPAH enable the binding of one or more Mg2+ ions in the active site and elsewhere on the protein surface. Notwithstanding these differences, activity assays with a panel of acetylpolyamine and acetyllysine substrates confirm that msAPAH is a broad-specificity polyamine deacetylase, much like mrAPAH. The broad substrate specificity contrasts with the narrow substrate specificity of zHDAC10, which is highly specific for N8-acetylspermidine hydrolysis. Notably, quaternary structural features govern the substrate specificity of msAPAH and mrAPAH, whereas tertiary structural features govern the substrate specificity of zHDAC10.

Melting Transitions of the Organic Subphase in Layered Two-Dimensional Halide Perovskites.

We investigate the phase behavior of two-dimensional (C xH2 x+1NH3)2[(MA,FA)PbI3] n-1PbI4 layered perovskites near room temperature (-20 °C to +100 °C) as a function of the octahedral layer thickness ( n = 1, 2, 3, 4), alkylammonium chain length (butyl, pentyl, and hexyl), and identity of the small organic cation (methylammonium and formamidinium). Using differential scanning calorimetry and X-ray diffraction, we observe a reversible first-order phase transition corresponding to a partial melting transition of the alkylammonium chains separating the perovskite layers. The melting temperature, Tm, increases from 10 to 77.9 to 95.9 °C as the carbon chain length increases from C4 to C5 to C6, but it is insensitive to octahedral layer thickness, n. The latent heat of melting, Δ Hm, was in the range of 3-5 kJ/mol-spacer, indicating only partial disordering of the carbon chain. We discuss these findings and their implications in the context of melting in other two-dimensional molecular systems.

Ultra-Stable Imidazolium-Based Anion Exchange Membranes for Alkaline Fuel Cell Applications

The development of cationic polymers for anion-exchange membranes (AEMs) with high alkaline stability and conductivity is a considerable challenge in materials chemistry. However, the commonly employed organic cations have limited alkaline stability, especially at high temperatures, which restricts the commercialization of AEM alkaline fuel cell technology. To address this problem, we have designed and synthesized a series of novel imidazolium-based AEMs for alkaline fuel cell applications. Degradation rates and mechanisms of small organic cations were analyzed by NMR spectroscopy and rationalized using density functional theory (DFT) calculations. The substituent selection at each position of the imidazolium ring has a dramatic effect on the overall cation stability, correlating to the stability profiles of corresponding AEMs. The most stable imidazoliums were chosen to polymerize robust AEMs, while their stability was examined by dynamic vapor sorption (DVS) technique, and conductivity was measured with the four-probe method. The results have shown the superior alkaline stability and conductivity of our imidazolium-based AEMs even at high temperature (80 °C), confirming they are promising AEM candidates for practical application in alkaline fuel cell.

General Synthesis Principles for Ruddlesden–Popper Hybrid Perovskite Halides from a Dynamic Equilibrium

Two-dimensional (2D) Ruddlesden–Popper hybrid perovskites are a homologous series of compounds with the formula A′2An–1BnX3n+1 (A′ = bulky organic cation; A = small organic cation; B = Pb2+ or Sn2+, X = Cl–, Br–, I–; n is an integer) composed of inorganic octahedral layers separated by organic spacer cations. The octahedral layer thickness is modified by the stoichiometry of the A-site cation, but limited methods exist for controlled and discriminating synthesis for all compositions. We report a general synthesis method and its principles that yield phase-pure 2D hybrid perovskites; the chemistry operates within a dynamic equilibrium established by the molar solubility of the compounds within the homologous series. A solvent–antisolvent (HI–acetic acid) pair and the common-ion effect provide selective control over the molar solubility to precipitate phase-pure compounds, as is supported by simple and predictive calculations. Here, this approach is demonstrated in detail with A′ = n-butylammonium, A = meth...

Nanostructured Mechanochemically Prepared Hybrid Perovskites Based on PbI2and Alkylammonium Halides for Optoelectronic Applications

The preparation of hybrid perovskites (HPs) with small and large organic cations with a solventless mechanochemical treatment of the mixture of lead iodide and alkylammonium halides is presented. X-ray diffraction and electron microscopy show that the use of the mechanochemical approach for synthesis of HPs with small cations (CH3NH3PbI2X, X = I, Br, Cl) leads to the formation of crystalline nanoparticles with uniform shapes and sizes that do not exceed 70 nm. At the same time, the mechanochemical synthesis of HPs with large organic cations, (C6H13NH3)2PbI2X2, induces the nanostructuration with the formation of 2D structures regardless of the stoichiometry of the initial reaction mixture. We show that our mechanochemically prepared HPs exhibit a photoluminescence whose colors depend on the size of the organic cations and the type of halide ions that could be used for different optoelectronic applications, for improving color rendering index of garnet-based white-light-emitting diodes in particular.

Guanidinium-Formamidinium Lead Iodide: A Layered Perovskite-Related Compound with Red Luminescence at Room Temperature.

Two-dimensional hybrid organic–inorganic lead halides perovskite-type compounds have attracted immense scientific interest due to their remarkable optoelectronic properties and tailorable crystal structures. In this work, we present a new layered hybrid lead halide, namely [CH(NH2)2][C(NH2)3]PbI4, wherein puckered lead-iodide layers are separated by two small and stable organic cations: formamidinium, CH(NH2)2+, and guanidinium, C(NH2)3+. This perovskite is thermally stable up to 255 °C, exhibits room-temperature photoluminescence in the red region with a quantum yield of 3.5%, and is photoconductive. This study highlights a vast structural diversity that exists in the compositional space typically used in perovskite photovoltaics.