LIGHT-DRIVEN ROTARY MOLECULAR MOTORS

1 . A method of using a compound as a molecular motor that can be driven by light to produce directional motion, comprising the step of:

introducing light to a compound to produce directional motion, where the compound is defined by Formula (1):

wherein:

C b is a carbocyclic or heterocyclic group wherein the atom within the cyclic structure is singly bound to A and selected from the group consisting of C, N, Si, and Sn;

A is CR, COR, CSR, CNR 2 , CCN, CCONR 2 , CNO 2 , CNNAr, CX′, or N, wherein Ar is aryl or heteroaryl and X′ is a halide;

R is H; substituted or unsubstituted, branched or straight chain C 1 -C 18 alkyl; substituted or unsubstituted, branched or straight chain C 2 -C 18 alkenyl; substituted or unsubstituted, branched or straight chain C 2 -C 18 alkynyl; —(OCH 2 CH 2 ) 1-15 OH; —(OC 3 H 6 ) 1-15 OH;

substituted or unsubstituted, saturated or unsaturated, carbocycles or heterocycles; or

substituted or unsubstituted aryl or heteroaryl; and

C r is a chromophore which has a substantially planar cyclic structure.

2 . A method of using a compound as a molecular motor that can be driven by light to produce directional motion, comprising the step of:

introducing light to a compound to produce directional motion, where the compound is defined by formula (2):

wherein:

C b is a carbocyclic or heterocyclic group wherein the atom within the cyclic structure is singly bound to A and selected from the group consisting C, N, Si, and Sn;

A is CR, COR, CSR, CNR 2 , CCN, CCONR 2 , CNO 2 , CNNAr, CX′, or N, wherein Ar is aryl or heteroaryl and X′ is a halide;

G is CR, CR 2 , C═CR 2 , C═O, C═S, C═NR, N, NR, O, or S;

n is 0, 1, or 2;

E is independently CH, CH 2 , N, NH, O, or S;

m is independently 0, 1, 2, or 3;

X is independently R 1 , SiR 1 3 , ═NR 1 , NR 1 2 , ═O, OR 1 , ═S, or SR 1 ;

Y is independently R 1 , SiR 1 3 , ═NR 1 , NR 1 2 , ═O, OR 1 , ═S, or SR 1 ;

q is independently 0, 1, 2, 3, or 4;

R is independently H;

substituted or unsubstituted, branched or straight chain C 1 -C 18 alkyl;

substituted or unsubstituted, branched or straight chain C 2 -C 18 alkenyl;

substituted or unsubstituted, branched or straight chain C 1 -C 18 alkynyl;

—(OCH 2 CH 2 ) 1-15 OH; —(OC 3 H 6 ) 1-15 OH;

substituted or unsubstituted, saturated or unsaturated, carbocycles or heterocycles; or

substituted or unsubstituted aryl or heteroaryl; and

R 1 is independently H;

substituted or unsubstituted, branched or straight chain C 1 -C 18 alkyl;

substituted or unsubstituted, branched or straight chain C 2 -C 18 alkenyl;

substituted or unsubstituted, branched or straight chain C 2 -C 18 alkynyl;

—(OCH 2 CH 2 ) 1-15 OH; —(OC 3 H 6 ) 1-15 OH;

substituted or unsubstituted, saturated or unsaturated, fused or unfused carbocycles

or heterocycles; or

substituted or unsubstituted, fused or unfused aryl or heteroaryl;

wherein when R 1 is a cyclic structure the heteroatoms Si, N, O, or S within the definitions of X and Y may form part of the cyclic structure.

3 . The method of claim 2 , wherein C b is a bi-cyclic carbocycle or heterocycle.

4 . The method of claim 2 , wherein C b is a tri-cyclic carbocycle or heterocycle.

5 . The method of claim 2 , wherein

A is CR or N;

G is CR, CR 2 , N, NR, O, or S;

n is 0 or 1;

E is independently CH, CH 2 , N, NH, O, or S;

m is independently 1 or 2;

X is independently R 1 , ═NR NR 1 2 , OR 1 , ═S, or SR 1 ;

Y is independently R 1 , ═NR 1 , NR 1 2 , ═O, OR 1 , ═S, or SR 1 ;

q is independently 0, 1, 2, 3, or 4;

R is independently H;

substituted or unsubstituted, branched or straight chain C 1 -C 9 alkyl;

substituted or unsubstituted, branched or straight chain C 2 -C 9 alkenyl;

substituted or unsubstituted, branched or straight chain C 2 -C 9 alkynyl;

—(OCH 2 CH 2 ) 1-7 OH; —(OC 3 H 6 ) 1-7 OH;

substituted or unsubstituted, saturated or unsaturated, carbocycles or heterocycles; or

substituted or unsubstituted aryl or heteroaryl; and

R 1 is independently H;

substituted or unsubstituted, branched or straight chain C 1 -C 9 alkyl;

substituted or unsubstituted, branched or straight chain C 2 -C 9 alkenyl;

substituted or unsubstituted, branched or straight chain C 2 -C 9 alkynyl;

—(OCH 2 CH 2 ) 1-7 OH; —(OC 3 H 6 ) 1-7 OH;

substituted or unsubstituted, saturated or unsaturated, fused or unfused carbocycles

or heterocycles; or

substituted or unsubstituted, fused or unfused aryl or heteroaryl;

wherein when R 1 is a cyclic structure the heteroatoms Si, N, O, or S within the definitions of X and Y may form part of the cyclic structure.

6 . The method of claim 5 , wherein

A is CR;

G is CR, CR 2 , N, or NR;

n is 0 or 1;

E is independently CH, CH 2 , N, or NH;

each m is 1;

X is independently R 1 , NR 1 2 , or OR 1 , or SR 1 ;

Y is independently R 1 , NR 1 2 , or OR 1 ;

q is independently 0, 1, or 2;

R is independently H;

substituted or unsubstituted, branched or straight chain C 1 -C 5 alkyl;

substituted or unsubstituted, branched or straight chain C 2 -C 5 alkenyl;

substituted or unsubstituted, branched or straight chain C 2 -C 5 alkynyl;

substituted or unsubstituted, saturated or unsaturated, carbocycle or heterocycle

selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,

pyrrolidinyl, piperidyl, imidazolidinyl, pyrazolidinyl, pyrazolinyl, piperazinyl, morpholinyl, chromanyl, indolinyl, and their corresponding iso-forms; or

substituted or unsubstituted fused or unfused aryl or heteroaryl selected from the group consisting of phenyl, benzyl, naphthyl, furyl, benzofuranyl, pyranyl, pyrazinyl, thienyl, pyrrolyl, imidazolyl, pyridyl, pyrimidinyl, pyridazinyl, indolyl, indolizinyl, indoazolyl, purinyl, quinolyl, thiazolyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzothienyl, anthryl, phenathtryl, and their corresponding iso-forms; and

R 1 is independently H;

substituted or unsubstituted, branched or straight chain C 1 -C 4 alkyl;

substituted or unsubstituted, branched or straight chain C 2 -C 4 alkenyl;

substituted or unsubstituted, branched or straight chain C 2 -C 4 alkynyl;

substituted or unsubstituted, saturated or unsaturated, fused or unfused carbocycles

or heterocycles selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidyl, imidazolidinyl, pyrazolidinyl, pyrazolinyl, piperazinyl, morpholinyl, chromanyl, indolinyl, and their corresponding iso-forms; or

substituted or unsubstituted fused or unfused aryl or heteroaryl selected from the group consisting of phenyl, benzyl, naphthyl, furyl, benzofuranyl, pyranyl, pyrazinyl, thienyl, pyrrolyl, imidazolyl, pyridyl, Pyrimidinyl, pyridazinyl, indolyl, indolizinyl, indoazolyl, purinyl, quinolyl, thiazolyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzothienyl, anthryl, phenathtryl, and their corresponding iso-forms.

7 . The method of claim 6 , wherein

A is CR;

G is CR, CR 2 , N, or NR;

n is 0 or 1;

E is independently CH, CH 2 , N, or NH;

each m is 1;

X is independently R 1 , NR 1 2 , or OR 1 ;

Y is independently R 1 , NR 1 2 , or OR 1 ;

q is independently 0, 1, or 2;

R is independently H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, or pyridinyl; and

R 1 is independently H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, or pyridinyl.

8 . The method of claim 2 , wherein the moiety of formula (2) defined by

is selected from the group consisting of 4H-cyclopenta-[def]phenanthrene, 7H-dibenzo[c,d]fluorene, 13H-dibenzo[a,i]fluorene, 13H-dibenzo[a,g]fluorene, 11H-benzo[a]fluorene, 7H-benzo[c]fluorene, and derivatives of hexafulvenes and heptafulvenes.

9 . The method of claim 2 , wherein formula (2) has the structure:

wherein Z is substituted or unsubstituted, branched or straight chain C 3 -C 9 alkylene; substituted or unsubstituted, branched or straight chain C 3 -C 9 alkenylene; substituted or unsubstituted, branched or straight chain C 3 -C 9 alkynylene; —(OCH 2 CH 2 ) 1-3 O—; —(OC 3 H 6 ) 1-3 O—; substituted or unsubstituted, saturated or unsaturated, divalent carbocycles or heterocycles; or substituted or unsubstituted arylene or heteroarylene.

10 . The method of claim 2 , wherein formula (2) has the structure: