Compositions, apparatus, systems, and methods for resolving electronic excited states
View Patent ↗The present disclosure relates, according to some embodiments, to molecules, including conjugated fused polycyclic molecules, that may receive excited state energy from other molecules (e.g., light-absorbing molecules) or directly from the irradiation sources. According to some embodiments, the disclosure relates to molecules, including conjugated fused polycyclic molecules, that may resolve (e.g., quench, dissipate) excited state energy, normally by way of releasing it as heat. (e.g., as heat). Conjugated fused polycyclic molecules of various structures are disclosed including Formula III: The disclosure further relates to methods of use and/or therapy using molecules of Formulas I, II, and/or III.
1. A conjugated fused polycyclic molecule having a structure according to Formula II:
wherein
A 1 is independently carbonyl, C═C(R 13 )R 14 , O, S, S═O, S(O)═O, C═S,
R 13 is independently nitrile, C(O)OR 15 , C(O)R 16 , C(O)N(R 17 )R 18 , C(O)—S—R 19 , aryl, substituted or fused aryl,
R 14 is independently nitrile, C(O)OR 20 , C(O)R 21 , C(O)N(R 22 )R 23 , C(O)—S—R 24 , aryl, substituted or fused aryl,
R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , and R 24 are each independently aryl, substituted aryl, fused aryl, alkyl, substituted alkyl, or branched alkyl,
A 2 is independently carbonyl, C═C(R 13 )R 14 , O, S, S═O, S(O)═O, C═S,
D 3 is independently H, hydroxyl, or R 25 ,
D 4 is independently H, hydroxyl, or R 26 , and
R 25 and R 26 are each independently alkyl, heteroalkyl, alkoxyl, heteroalkoxyl, aryl, heteroaryl, or fused aryl,
provided that
at least one of A 1 and A 2 is C═C(R 13 )R 14 ,
if neither A 1 nor A 2 is S, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is nitrile,
if neither A 1 nor A 2 is O, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is C(O)OR 15/20 ,
if both A 1 and A 2 are C═C(R 13 )R 14 , then R 15 and R 20 ≠ alkyl, substituted alkyl, or branched alkyl,
if A 1 =O and A 2 =C═C(R 13 )R 14 , then D 3 ≠D 4 ,
if A 1 =O, A 2 =C═C(R 13 )R 14 and R 13 ═C(O)OR 15 , then R 14 ≠ C(O)OR 20 ;
if A 1 =O, A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)R 16 , then R 14 ≠ C(O)R 21 ;
if A 1 =S, A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)R 16 , then R 14 ≠ C(O)R 21 , and
if either A 1 or A 2 is S, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is nitrile, wherein the conjugated fused polycyclic molecule is configured (a) to resolve at least one excited state of a photoactive molecule substantially without observable photochemical reaction, (b) to resolve at least one excited state of a photoactive molecule substantially non-radiatively, or (c) to resolve at least one excited state of a photoactive molecule substantially without observable photochemical reaction and substantially non-radiatively.
2. A conjugated fused polycyclic molecule according to claim 1 , wherein each R 13 and R 14 are different from each other.
3. A conjugated fused polycyclic molecule according to claim 1 , wherein D 3 and D 4 are hydrogen.
4. A conjugated fused polycyclic molecule according to claim 1 , wherein at least one of R 15 , R 16 , R 17 , R 18 , R19, R 20 , R 21 , R 22 , R 23 , and R 24 is an alkyl group having from about 1 to about 30 carbon atoms.
5. A conjugated fused polycyclic molecule according to claim 1 , wherein one of R 13 and R 14 is nitrile.
6. A conjugated fused polycyclic molecule according to claim 1 , wherein neither R 13 nor R 14 is nitrile.
7. A conjugated fused polycyclic molecule according to claim 1 , wherein the conjugated fused polycyclic molecule comprises no more than 6 rings with no more than 4 of these rings fused to each other.
8. A paint, a coating, a cosmetic, a sunscreen, a pharmaceutical preparation, a bituminous preparation, an ink, a toner, a photographic emulsion, a glass, or a fabric comprising a composition according to claim 1 .
9. A conjugated fused polycyclic molecule having a structure according to Formula II:
wherein
A 1 is independently carbonyl, C═C(R 13 )R 14 , O, S, S═O, S(O)═O, C═S,
R 13 is independently nitrile, C(O)R 16 , C(O)N(R 17 )R 18 , C(O)—S—R 19 , aryl, substituted or fused aryl,
R 14 is independently nitrile, C(O)R 21 , C(O)N(R 22 )R 23 , C(O)-S-R 24 , aryl, substituted or fused aryl,
R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , and R 24 are each independently aryl, substituted aryl, fused aryl, alkyl, substituted alkyl, or branched alkyl,
A 2 is independently carbonyl, C═C(R 13 )R 14 , O, S, S═O, S(O)═O, C═S,
D 3 is independently H, hydroxyl, or R 25 ,
D 4 is independently H, hydroxyl, or R 26 , and
R 25 and R 26 are each independently alkyl, heteroalkyl, alkoxyl, heteroalkoxyl, aryl, heteroaryl, or fused aryl,
provided that
at least one of A 1 and A 2 is C═C(R 13 )R 14 ,
if neither A 1 nor A 2 is S, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is nitrile,
if A 1 =O and A 2 =C═C(R 13 )R 14 , then D 3 ≠D 4 ,
if A 1 =O A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)OR 15 , then R 14 ≠C(O)OR 20 ;
if A 1 =O A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)R 16 , then R 14 ≠C(O)R 21 ;
if A 1 =S A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)R 16 then R 14 ≠C(O)R 21 and
if either A 1 or A 2 is S, for each C═C(R 13 )R 14 ,no more than one of R 13 and R 14 is nitrile,
wherein the conjugated fused polycyclic molecule is configured (a) to resolve at least one excited state of a photoactive molecule substantially without observable photochemical reaction, (b) to resolve at least one excited state of a photoactive molecule substantially non-radiatively, or (c) to resolve at least one excited state of a photoactive molecule substantially without observable photochemical reaction and substantially non-radiatively.
10. A conjugated fused polycyclic molecule having a structure according to Formula II:
wherein
A 1 is independently carbonyl, C═C(R 13 )R 14 O, S, S═O, S(O)═O, C═S,
R 13 is independently nitrile, C(O)OR 15 , C(O)R 16 , C(O)N(R 17 )R 18 , C(O)—S—R 19 , aryl, substituted or fused aryl,
R 14 is independently nitrile, C(O)OR 20 , C(O)R 21 , C(O)N(R 22 )R 23 , C(O)—S—R 24 , aryl, substituted or fused aryl,
R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , and R 24 are each independently aryl, substituted aryl, fused aryl, alkyl, substituted alkyl, or branched alkyl,
A 2 is independently carbonyl, C═C(R 13 )R 14 , O, S, S═O, S(O)═O, C═S,
D 3 is independently H, hydroxyl, or R 25 ,
D 4 is independently H, hydroxyl, or R 26 , and
R 25 and R 26 are each independently alkyl, heteroalkyl, alkoxyl, heteroalkoxyl, aryl, heteroaryl, or fused aryl,
provided that
at least one of A 1 and A 2 is C═C(R 13 )R 14 ,
if neither A 1 nor A 2 is S, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is nitrile,
if either A 1 or A 2 is O, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is C(O)OR 15/20 ,
if R 13 is C(O)OR 15 , R 15 ≠ alkyl,
if R 14 is C(O)OR 20 , R 20 ≠ alkyl,
if A 1 =O and A 2 =C═C(R 13 )R 14 , then D 3 ≠D 4 ,
if A 1 =O, A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)OR 15 , then R 14 ≠C(O)OR 20 ;
if A 1 =O, A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)R 16 , then R 14 ≠ C(O)R 21 ;
if A 1 =S, A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)R 16 , then R 14 ≠C(O)R 21 , and
if either A 1 or A 2 is S, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is nitrile,
wherein the conjugated fused polycyclic molecule is configured (a) to resolve at least one excited state of a photoactive molecule substantially without observable photochemical reaction, (b) to resolve at least one excited state of a photoactive molecule substantially non-radiatively, or (c) to resolve at least one excited state of a photoactive molecule substantially without observable photochemical reaction and substantially non-radiatively.
11. A conjugated fused polycyclic molecule having a structure according to Formula II:
wherein
A 1 is independently carbonyl, C═C(R 13 )R 14 , O, S, S═O, S(O)═O, C═S,
R 13 is independently nitrile, C(O)OR 15 , C(O)R 16 , C(O)N(R 17 )R 18 , C(O)—S—R 19 , aryl, substituted or fused aryl,
R 14 is independently nitrile, C(O)OR 20 , C(O)R 21 , C(O)N(R 22 )R 23 , C(O)—S—R 24 , aryl, substituted or fused aryl,
R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , and R 24 are each independently aryl, substituted aryl, fused aryl, alkyl, substituted alkyl, or branched alkyl,
A 2 is independently carbonyl, C═C(R 13 )R 14 , O, S, S═O, S(O)═O, C═S,
D 3 is independently H, hydroxyl, or R 25 ,
D 4 is independently H, hydroxyl, or R 26 , and
R 25 and R 26 are each independently alkyl, heteroalkyl, alkoxyl, heteroalkoxyl, aryl, heteroaryl, or fused aryl,
provided that
at least one of A 1 and A 2 is C═C(R 13 )R 14 ,
if neither A 1 nor A 2 is S, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is nitrile, and
if either A 1 or A 2 is O, for each C═C(R R13 )R 14 , no more than one of R 13 and R 14 is C(O)OR 15/20 ,
if R 13 is C(O)OR 15 and R 15 =alkyl, then R 15 ≠ ethyl,
if R 14 is C(O)OR 20 and R 20 =alkyl, then R 20 ≠ ethyl,
if A 1 =O and A 2 =C═C(R 13 )R 14 , then D 3 ≠ D 4 ,
if A 1 =O, A 2 =C═C(R 13 )R 14 , and R 13 ═C(O)OR 15 , then R 14 C(O)OR 20 ;
if A 1 =O, A 2 =C═C(R 13 ) 14 , and R 13 ═C(O)R 16 , then R 14 ≠C(O)R 21 ;
if A 1 =S, A 2 =C═C(R 13 )R 14 ,and R 13 ═C(O)R 16 , then R 14 ≠C(O)R 21 , and
if either A 1 or A 2 is S, for each C═C(R 13 )R 14 , no more than one of R 13 and R 14 is nitrile,
wherein the conjugated fused polycyclic molecule is configured (a) to resolve at least one excited state of a photoactive molecule substantially without observable photochemical reaction, (b) to resolve at least one excited state of a photoactive molecule substantially non-radiatively, or (c) to resolve at least one excited state of a photoactive molecule substantially without observable photochemical reaction and substantially non-radiatively.