ABSTRACT
Donor−acceptor (D−A) small molecules are regarded as promising hole-transporting materials for perovskite solar cells (PSCs) due to their tunable optoelectronic properties. This paper reports the design, synthesis and characterization of three novel isomeric D-π-A small molecules PY1, PY2 and PY3. The chemical structures of the molecules consist of a pyrazolo[1,5-a]pyrimidine acceptor core functionalized with one 3,6-bis(4,4'-dimethoxydiphenylamino)carbazole (3,6-CzDMPA) donor moiety via a phenyl π-spacer at the 3, 5 and 7 positions, respectively. The isolated compounds possess suitable energy levels, sufficient thermal stability (Td > 400 °C), molecular glass behavior with Tg values in the range of 127−136 °C slightly higher than that of the reference material Spiro-OMeTAD (126 °C) and acceptable hydrophobicity. Undoped PY1 demonstrates the highest hole mobility (3 × 10−6 cm2 V−1 s−1) compared to PY2 and PY3 (1.3 × 10−6 cm2 V−1 s−1). The whole isomers were incorporated as doped HTMs in planar n-i-p PSCs based on double cation perovskite FA0.85Cs0.15Pb(I0.85Br0.15)3. The non-optimized device fabricated using PY1 exhibited a power conversion efficiency (PCE) of 12.41%, similar to that obtained using the reference, Spiro-OMeTAD, which demonstrated a maximum PCE of 12.58% under the same conditions. The PY2 and PY3 materials demonstrated slightly lower performance in device configuration, with relatively moderate PCEs of 10.21% and 10.82%, respectively, and slight hysteresis behavior (−0.01 and 0.02). The preliminary stability testing of PSCs is also described. The PY1-based device exhibited better stability than the device using Spiro-OMeTAD, which could be related to its slightly superior hydrophobic character preventing water diffusion into the perovskite layer.
ABSTRACT
The title compound, C(20)H(31)NO(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five-and ten-membered rings with the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the six-membered ring display a chair conformation and the five-membered ring an envelope conformation with the C(H)-C-C(H) atom at the flap. The dihedral angle between the ten-membered ring and the lactone ring is 21.7â (4)°. The mol-ecular conformation is stabilized by an O-Hâ¯N hydrogen bond and the crystal structure is stabilized by weak inter-molecular C-Hâ¯O inter-actions.
ABSTRACT
The title compound, C(16)H(24)O(3), was synthesized from ilicic acid, which was isolated from the aerial part of Inula viscosa- (L) Aiton [or Dittrichia viscosa- (L) Greuter]. The asymmetric unit contains two independent mol-ecules, in each of which the seven-membered ring shows a chair conformation, whereas the five-membered ring presents disorder. In the two molecules, three C atoms in the five-membered ring are disordered over two positions with site-occupancy factors of 0.53/0.47 and 0.83/0.17. The dihedral angle between the two rings is different in the two mol-ecules [31.7â (3) and 47.7â (7)°]. The crystal structure is stabilized by weak inter-molecular C-Hâ¯O hydrogen-bond inter-actions.
ABSTRACT
The title compound, C(19)H(29)NO(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo-[9.3.0.0(2),(4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from two fused five- and ten-membered rings with the (morpholin-4-yl)methyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and the morpholine rings display approximate chair-chair and chair conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 27.93â (6)°. The crystal structure is stabilized by weak inter-molecular C-Hâ¯O hydrogen-bond inter-actions. An intra-molecular O-Hâ¯N hydrogen bond also occurs.
ABSTRACT
The title compound, C(15)H(20)O(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The seven-membered ring has a chair conformation, while the five-membered rings display twisted conformations. The dihedral angle between the seven-membered ring and the lactone ring is 21.69â (10)°. In the crystal, mol-ecules are linked into chains propagating along the c axis by inter-molecular O-Hâ¯O hydrogen bonds; an intra-molecular O-Hâ¯O link also occurs.
ABSTRACT
The title compound, C(15)H(18)O(3), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The five-membered lactone ring has a twisted conformation, while the six- and five-membered rings display chair and envelope conformations, respectively. The dihedral angle between the two five-membered rings is 50.57â (11)°.
ABSTRACT
The title compound, C(21)H(26)O, was semisynthesized from isocostic acid, isolated from the aerial part of Inula Viscosa- (L) Aiton [or Dittrichia Viscosa- (L) Greuter]. The cyclo-hexene ring has a half-chair conformation, whereas the cyclo-hexane ring displays a chair conformation.
ABSTRACT
The title compound, C(14)H(24)O(2), was synthesized from ilicic acid, which was isolated from the aerial part of Inula Viscosa- (L) Aiton [or Dittrichia Viscosa- (L) Greuter]. The mol-ecule contains two fused six-membered rings, which both display a chair conformation. In the crystal, mol-ecules are linked into chains propagating along the b axis by inter-molecular O-Hâ¯O hydrogen bonds.
ABSTRACT
The title compound, C(15)H(21)ClO(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five- and ten-membered rings. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325â (15)â Å from the mean plane through the remaining four atoms, whereas the ten-membered ring displays an approximate chair-chair conformation. The dihedral angle between the two rings is 66.4â (2)°. In the crystal, mol-ecules are linked into chains propagating along the a axis by O-Hâ¯O hydrogen bonds.
ABSTRACT
The title compound, C(25)H(34)N(2)O(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule contains a fused five- and ten-membered ring system. The ten-membered ring adopts an approximate chair-chair conformation, while the five-membered ring is in an envelope conformation, with the C atom closest to the hy-droxy group forming the flap. The piperazine ring is in a chair conformation. In the crystal, O-Hâ¯O hydrogen bonds connect mol-ecules into chains along [100]. Weak inter-molecular C-Hâ¯O hydrogen bonds are also present.
ABSTRACT
The title compound, C(20)H(31)NO(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo-[9.3.0.0(2),(4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five-and ten-membered rings with the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the six- and five-membered rings display chair and envelope conformations, respectively. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 20.8â (3)°. An intra-molecular O-Hâ¯N hydrogen-bond occurs. The crystal structure is stabilized by weak inter-molecular C-Hâ¯O hydrogen bonds.
ABSTRACT
THE TITLE COMPOUND [SYSTEMATIC NAME: 2-(4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octa-hydro-naphthalen-2-yl)acrylic acid anhydride], C(30)H(42)O(3), is a new isocostic anhydride which was synthesized from the aerial part of Inula Viscosa- (L) Aiton [or Dittrichia Viscosa- (L) Greuter]. The mol-ecule adopts an essentially linear shape with two terminal fused-rings bridged by the anhydride group. The external rings have the same conformation (half-chair) while each of the two inner rings has an almost ideal chair conformation. In the crystal, inter-molecular C-Hâ¯O inter-actions link the mol-ecules into a two-dimensional array in the bc plane.
ABSTRACT
The title compound, C(18)H(20)O(3), a hemisynthetic product, was obtained by the reaction of benzoyl chloride and p-methoxy-thymol. The structure comprises two benzene rings bridged by a carboxyl group; the dihedral angle between the rings is 73.54â (8)°.
ABSTRACT
The title compound, C(23)H(31)NO, was semisynthesized from isocostic acid, isolated from the aerial part of Inula Viscosa- (L) Aiton [or Dittrichia Viscosa- (L) Greuter]. The cyclo-hexene ring has a half-chair conformation, whereas the cyclo-hexane ring displays a chair conformation. The dihedral angle between the latter ring and its substituent is 83.6â (7)°.
